diff --git a/dictation_client/src/AppRouter.tsx b/dictation_client/src/AppRouter.tsx
index 7abc3ca..68d22ed 100644
--- a/dictation_client/src/AppRouter.tsx
+++ b/dictation_client/src/AppRouter.tsx
@@ -2,7 +2,6 @@ import { Route, Routes } from "react-router-dom";
 import TopPage from "pages/TopPage";
 import AuthPage from "pages/AuthPage";
 import LoginPage from "pages/LoginPage";
-import SamplePage from "pages/SamplePage";
 import { AuthErrorPage } from "pages/ErrorPage";
 import { NotFoundPage } from "pages/ErrorPage/notFound";
 import { RouteAuthGuard } from "components/auth/routeAuthGuard";
@@ -53,11 +52,6 @@ const AppRouter: React.FC = () => (
       path="/license"
       element={<RouteAuthGuard component={<LicensePage />} />}
     />
-    <Route
-      path="/xxx"
-      element={<RouteAuthGuard component={<SamplePage />} />}
-    />
-    {/* XXX ヘッダーの挙動確認のため仮のページを作成 */}
     <Route
       path="/account"
       element={<RouteAuthGuard component={<AccountPage />} />}
diff --git a/dictation_client/src/components/auth/constants.ts b/dictation_client/src/components/auth/constants.ts
index cf2b972..ef98041 100644
--- a/dictation_client/src/components/auth/constants.ts
+++ b/dictation_client/src/components/auth/constants.ts
@@ -39,6 +39,12 @@ export const UNAUTHORIZED_TO_CONTINUE_ERROR_CODES = [
   "E010501",
 ];
 
+/**
+ * ローカルストレージに残すキー類
+ * @const {string[]}
+ */
+export const KEYS_TO_PRESERVE = ["accessToken", "refreshToken", "displayInfo"];
+
 /**
  * アクセストークンを更新する基準の秒数
  * @const {number}
diff --git a/dictation_client/src/components/delegate/index.tsx b/dictation_client/src/components/delegate/index.tsx
index 1bfce9e..a4750de 100644
--- a/dictation_client/src/components/delegate/index.tsx
+++ b/dictation_client/src/components/delegate/index.tsx
@@ -46,6 +46,7 @@ export const DelegationBar: React.FC = (): JSX.Element => {
         alt="Exit"
         title="Exit"
         onClick={onClickExit}
+        data-tag="exit-delegation"
       />
     </div>
   );
diff --git a/dictation_client/src/components/header/constants.ts b/dictation_client/src/components/header/constants.ts
index 66a2665..7dc14fe 100644
--- a/dictation_client/src/components/header/constants.ts
+++ b/dictation_client/src/components/header/constants.ts
@@ -7,7 +7,6 @@ export const HEADER_MENUS_LICENSE = "License";
 export const HEADER_MENUS_DICTATIONS = "Dictations";
 export const HEADER_MENUS_WORKFLOW = "Workflow";
 export const HEADER_MENUS_PARTNER = "Partners";
-export const HEADER_MENUS_XXX = "XXX"; // XXX 仮のタブ
 
 export const HEADER_MENUS: {
   key: HeaderMenus;
@@ -44,7 +43,6 @@ export const HEADER_MENUS: {
     label: getTranslationID("common.label.headerPartners"),
     path: "/partners",
   },
-  { key: HEADER_MENUS_XXX, label: "xxx", path: "/xxx" }, // XXX 仮のタブ
 ];
 
 export const HEADER_NAME = getTranslationID("common.label.headerName");
diff --git a/dictation_client/src/components/header/loginedHeader.tsx b/dictation_client/src/components/header/loginedHeader.tsx
index 86f5e68..57ee5dd 100644
--- a/dictation_client/src/components/header/loginedHeader.tsx
+++ b/dictation_client/src/components/header/loginedHeader.tsx
@@ -87,6 +87,7 @@ const LoginedHeader: React.FC<HeaderProps> = (props: HeaderProps) => {
                     ? styles.isActive
                     : ""
                 }
+                data-tag={`menu-${x.key}`}
               >
                 {t(x.label)}
               </a>
@@ -101,6 +102,7 @@ const LoginedHeader: React.FC<HeaderProps> = (props: HeaderProps) => {
           <span
             className={styles.accountSignout}
             onClick={onSignoutButton}
+            data-tag="logout"
             style={{ pointerEvents: isDelegation ? "none" : "auto" }}
           >
             <img src={logout} alt="" className={styles.accountIcon} />
diff --git a/dictation_client/src/components/header/types.ts b/dictation_client/src/components/header/types.ts
index f80bbe9..622b15b 100644
--- a/dictation_client/src/components/header/types.ts
+++ b/dictation_client/src/components/header/types.ts
@@ -8,8 +8,7 @@ export type HeaderMenus =
   | "License"
   | "Dictations"
   | "Workflow"
-  | "Partners"
-  | "XXX";
+  | "Partners";
 
 // ログイン後に遷移しうるパス
 export type LoginedPaths =
@@ -18,5 +17,4 @@ export type LoginedPaths =
   | "/license"
   | "/dictations"
   | "/workflow"
-  | "/partners"
-  | "/xxx";
+  | "/partners";
diff --git a/dictation_client/src/components/header/utils.ts b/dictation_client/src/components/header/utils.ts
index 937786e..10aa168 100644
--- a/dictation_client/src/components/header/utils.ts
+++ b/dictation_client/src/components/header/utils.ts
@@ -20,7 +20,6 @@ export const isLoginPaths = (d: string): d is LoginedPaths => {
     case "/dictations":
     case "/workflow":
     case "/partners":
-    case "/xxx":
       return true;
     default: {
       // eslint-disable-next-line @typescript-eslint/no-unused-vars
diff --git a/dictation_client/src/components/snackbar/index.tsx b/dictation_client/src/components/snackbar/index.tsx
index 2f41161..0967d86 100644
--- a/dictation_client/src/components/snackbar/index.tsx
+++ b/dictation_client/src/components/snackbar/index.tsx
@@ -39,22 +39,34 @@ const Snackbar: React.FC<SnackbarProps> = (props) => {
   const isShow = isOpen ? styles.isShow : "";
 
   return (
-    <div className={`${styles.snackbar} ${isAlert} ${isShow}`}>
+    <div
+      className={`${styles.snackbar} ${isAlert} ${isShow}`}
+      data-tag="snackbar"
+    >
       {level === "error" ? (
-        <img src={reportWhite} className={styles.snackbarIcon} alt="check" />
+        <img
+          src={reportWhite}
+          className={styles.snackbarIcon}
+          alt="check"
+          data-tag="snackbar-error"
+        />
       ) : (
         <img
           src={checkCircleWhite}
           className={styles.snackbarIcon}
           alt="report"
+          data-tag="snackbar-report"
         />
       )}
-      <p className={styles.txNormal}>{message}</p>
+      <p className={styles.txNormal} data-tag="snackbar-text">
+        {message}
+      </p>
       {level === "error" && (
         <button
           style={{ marginLeft: "auto" }}
           type="button"
           onClick={onCloseSnackbar}
+          data-tag="close-snackbar"
         >
           <img
             src={closeWhite}
diff --git a/dictation_client/src/features/account/selectors.ts b/dictation_client/src/features/account/selectors.ts
index 23a0bfe..e99fdc1 100644
--- a/dictation_client/src/features/account/selectors.ts
+++ b/dictation_client/src/features/account/selectors.ts
@@ -1,4 +1,4 @@
-import { Dealer } from "api/api";
+import { Dealer, User } from "api/api";
 import { RootState } from "app/store";
 
 export const selectAccountInfo = (state: RootState) =>
@@ -10,7 +10,8 @@ export const selectDealers = (state: RootState) => {
   const { country } = state.account.domain.getAccountInfo.account;
   return dealers.filter((x: Dealer) => x.country === country);
 };
-export const selectUsers = (state: RootState) => state.account.domain.users;
+export const selectUsers = (state: RootState) =>
+  state.account.domain.users.filter((x: User) => x.emailVerified);
 export const selectIsLoading = (state: RootState) =>
   state.account.apps.isLoading;
 export const selectUpdateAccountInfo = (state: RootState) =>
diff --git a/dictation_client/src/features/auth/utils.ts b/dictation_client/src/features/auth/utils.ts
index edfd3c2..a296ff9 100644
--- a/dictation_client/src/features/auth/utils.ts
+++ b/dictation_client/src/features/auth/utils.ts
@@ -81,7 +81,9 @@ export const isAdminUser = (): boolean => {
   if (!token) {
     return false;
   }
-  return token.role.includes(ADMIN_ROLES.ADMIN);
+  // token.roleを" "で分割して配列にする
+  const role = token.role.split(" ");
+  return role.includes(ADMIN_ROLES.ADMIN);
 };
 
 /**
@@ -95,7 +97,9 @@ export const isStandardUser = (): boolean => {
   if (!token) {
     return false;
   }
-  return token.role.includes(ADMIN_ROLES.STANDARD);
+  // token.roleを" "で分割して配列にする
+  const role = token.role.split(" ");
+  return role.includes(ADMIN_ROLES.STANDARD);
 };
 
 /**
@@ -108,7 +112,9 @@ export const isAuthorUser = (): boolean => {
   if (!token) {
     return false;
   }
-  return token.role.includes(USER_ROLES.AUTHOR);
+  // token.roleを" "で分割して配列にする
+  const role = token.role.split(" ");
+  return role.includes(USER_ROLES.AUTHOR);
 };
 
 /**
@@ -132,5 +138,8 @@ export const isTypistUser = (): boolean => {
   if (!token) {
     return false;
   }
-  return token.role.includes(USER_ROLES.TYPIST);
+  // token.roleを" "で分割して配列にする
+  const role = token.role.split(" ");
+  // roleの中に"typist"が含まれているかどうかを返す
+  return role.includes(USER_ROLES.TYPIST);
 };
diff --git a/dictation_client/src/features/login/operations.ts b/dictation_client/src/features/login/operations.ts
index ffbf4e9..08a3a06 100644
--- a/dictation_client/src/features/login/operations.ts
+++ b/dictation_client/src/features/login/operations.ts
@@ -1,6 +1,7 @@
 import { createAsyncThunk } from "@reduxjs/toolkit";
 import type { RootState } from "app/store";
-import { getAccessToken, setToken } from "features/auth";
+import { setToken } from "features/auth";
+import { KEYS_TO_PRESERVE } from "components/auth/constants";
 import {
   AuthApi,
   UsersApi,
@@ -42,7 +43,18 @@ export const loginAsync = createAsyncThunk<
         refreshToken: data.refreshToken,
       })
     );
+    // ローカルストレージに残すキー
+    const keysToPreserve = KEYS_TO_PRESERVE;
 
+    // すべてのローカルストレージキーを取得
+    const allKeys = Object.keys(localStorage);
+
+    // 特定のキーを除外して削除
+    allKeys.forEach((key) => {
+      if (!keysToPreserve.includes(key)) {
+        localStorage.removeItem(key);
+      }
+    });
     return data;
   } catch (e) {
     // e ⇒ errorObjectに変換"
diff --git a/dictation_client/src/pages/AccountPage/deleteAccountPopup.tsx b/dictation_client/src/pages/AccountPage/deleteAccountPopup.tsx
index 2fcb13c..54aa4d2 100644
--- a/dictation_client/src/pages/AccountPage/deleteAccountPopup.tsx
+++ b/dictation_client/src/pages/AccountPage/deleteAccountPopup.tsx
@@ -56,7 +56,11 @@ export const DeleteAccountPopup: React.FC<DeleteAccountPopupProps> = (
       <div className={styles.modalBox}>
         <p className={styles.modalTitle}>
           {t(getTranslationID("deleteAccountPopup.label.title"))}
-          <button type="button" onClick={closePopup}>
+          <button
+            type="button"
+            onClick={closePopup}
+            data-tag="close-delegate-popup"
+          >
             <img src={close} className={styles.modalTitleIcon} alt="close" />
           </button>
         </p>
@@ -92,6 +96,7 @@ export const DeleteAccountPopup: React.FC<DeleteAccountPopupProps> = (
                 )}
                 className={`${styles.formDelete} ${styles.marginBtm1} ${styles.isActive}`}
                 onClick={onDeleteAccount}
+                data-tag="delete-account"
               />
               <p>
                 <input
@@ -102,6 +107,7 @@ export const DeleteAccountPopup: React.FC<DeleteAccountPopupProps> = (
                   )}
                   className={`${styles.formButtonTx} ${styles.marginBtm1}`}
                   onClick={closePopup}
+                  data-tag="cancel-delete-account"
                 />
               </p>
             </dd>
diff --git a/dictation_client/src/pages/AccountPage/index.tsx b/dictation_client/src/pages/AccountPage/index.tsx
index 924048c..79963ae 100644
--- a/dictation_client/src/pages/AccountPage/index.tsx
+++ b/dictation_client/src/pages/AccountPage/index.tsx
@@ -364,6 +364,7 @@ const AccountPage: React.FC = (): JSX.Element => {
                     }
                 `}
                     onClick={onSaveChangesButton}
+                    data-tag="savechanges-account"
                   />
                   <img
                     style={{ display: isLoading ? "inline" : "none" }}
@@ -377,7 +378,11 @@ const AccountPage: React.FC = (): JSX.Element => {
                 <ul className={styles.linkBottom}>
                   <li>
                     {/* eslint-disable-next-line jsx-a11y/click-events-have-key-events, jsx-a11y/no-static-element-interactions */}
-                    <a className={styles.linkTx} onClick={onDeleteAccountOpen}>
+                    <a
+                      className={styles.linkTx}
+                      onClick={onDeleteAccountOpen}
+                      data-tag="open-delete-account-popup"
+                    >
                       {t(getTranslationID("accountPage.label.deleteAccount"))}
                     </a>
                   </li>
diff --git a/dictation_client/src/pages/LoginPage/index.tsx b/dictation_client/src/pages/LoginPage/index.tsx
index e395607..e298c40 100644
--- a/dictation_client/src/pages/LoginPage/index.tsx
+++ b/dictation_client/src/pages/LoginPage/index.tsx
@@ -1,7 +1,14 @@
 import { useMsal } from "@azure/msal-react";
 import { AppDispatch } from "app/store";
 import { isIdToken } from "common/token";
-import { loadAccessToken, loadRefreshToken } from "features/auth";
+import {
+  clearToken,
+  isAdminUser,
+  isApproveTier,
+  isStandardUser,
+  loadAccessToken,
+  loadRefreshToken,
+} from "features/auth";
 import { loginAsync, selectLocalStorageKeyforIdToken } from "features/login";
 import React, { useCallback, useEffect } from "react";
 import Footer from "components/footer";
@@ -10,6 +17,7 @@ import { useTranslation } from "react-i18next";
 import { useDispatch, useSelector } from "react-redux";
 import { useNavigate } from "react-router-dom";
 import { isErrorObject } from "common/errors";
+import { TIERS } from "components/auth/constants";
 
 const LoginPage: React.FC = (): JSX.Element => {
   const { instance } = useMsal();
@@ -51,7 +59,29 @@ const LoginPage: React.FC = (): JSX.Element => {
         document.body.appendChild(a);
         a.click();
         document.body.removeChild(a);
-        navigate("/xxx");
+        // 第一～第四階層の管理者はライセンス画面へ遷移
+        if (
+          isApproveTier([TIERS.TIER1, TIERS.TIER2, TIERS.TIER3, TIERS.TIER4]) &&
+          isAdminUser()
+        ) {
+          navigate("/license");
+          return;
+        }
+        // 第五階層の管理者はユーザー画面へ遷移
+        if (isApproveTier([TIERS.TIER5]) && isAdminUser()) {
+          navigate("/user");
+          return;
+        }
+        // 一般ユーザーはdictationPageへ遷移
+        if (isStandardUser()) {
+          navigate("/dictations");
+          return;
+        }
+        // それ以外は認証エラー画面へ遷移
+        instance.logoutRedirect({
+          postLogoutRedirectUri: "/AuthError",
+        });
+        clearToken();
       }
     },
     [dispatch, i18n.language, instance, navigate]
diff --git a/dictation_client/src/pages/SamplePage/index.tsx b/dictation_client/src/pages/SamplePage/index.tsx
deleted file mode 100644
index b048ff6..0000000
--- a/dictation_client/src/pages/SamplePage/index.tsx
+++ /dev/null
@@ -1,39 +0,0 @@
-import { useMsal } from "@azure/msal-react";
-import { AppDispatch } from "app/store";
-import { UpdateTokenTimer } from "components/auth/updateTokenTimer";
-import Footer from "components/footer";
-import Header from "components/header";
-import { clearToken } from "features/auth";
-import { clearUserInfo } from "features/login";
-
-import React from "react";
-import { useDispatch } from "react-redux";
-import styles from "styles/app.module.scss";
-
-const SamplePage: React.FC = (): JSX.Element => {
-  const { instance } = useMsal();
-  const dispatch: AppDispatch = useDispatch();
-
-  return (
-    <div className={styles.wrap}>
-      <Header />
-      <UpdateTokenTimer />
-      <div>
-        <button
-          type="button"
-          className={styles.buttonText}
-          onClick={() => {
-            instance.logoutRedirect({ postLogoutRedirectUri: "/" });
-            dispatch(clearToken());
-            dispatch(clearUserInfo());
-          }}
-        >
-          sign out
-        </button>
-      </div>
-      <Footer />
-    </div>
-  );
-};
-
-export default SamplePage;
diff --git a/dictation_client/src/pages/TermsPage/index.tsx b/dictation_client/src/pages/TermsPage/index.tsx
index 586b029..cb45b5d 100644
--- a/dictation_client/src/pages/TermsPage/index.tsx
+++ b/dictation_client/src/pages/TermsPage/index.tsx
@@ -109,6 +109,7 @@ const TermsPage: React.FC = (): JSX.Element => {
                       target="_blank"
                       className={styles.linkTx}
                       onClick={() => setIsClickedEulaLink(true)}
+                      data-tag="open-eula"
                     >
                       {t(getTranslationID("termsPage.label.linkOfEula"))}
                     </a>
@@ -123,6 +124,7 @@ const TermsPage: React.FC = (): JSX.Element => {
                         value=""
                         onChange={(e) => setIsCheckedEula(e.target.checked)}
                         disabled={!isClickedEulaLink}
+                        data-tag="accept-eula"
                       />
                       {t(
                         getTranslationID("termsPage.label.checkBoxForConsent")
@@ -140,6 +142,7 @@ const TermsPage: React.FC = (): JSX.Element => {
                         target="_blank"
                         className={styles.linkTx}
                         onClick={() => setIsClickedDpaLink(true)}
+                        data-tag="open-dpa"
                       >
                         {t(getTranslationID("termsPage.label.linkOfDpa"))}
                       </a>
@@ -154,6 +157,7 @@ const TermsPage: React.FC = (): JSX.Element => {
                           value=""
                           onChange={(e) => setIsCheckedDpa(e.target.checked)}
                           disabled={!isClickedDpaLink}
+                          data-tag="accept-dpa"
                         />
                         {t(
                           getTranslationID("termsPage.label.checkBoxForConsent")
@@ -172,6 +176,7 @@ const TermsPage: React.FC = (): JSX.Element => {
                         canClickButton() ? styles.isActive : ""
                       }`}
                       onClick={onAcceptTermsOfUse}
+                      data-tag="accept-terms"
                     />
                   </p>
                 </dd>
diff --git a/dictation_client/src/pages/TopPage/index.tsx b/dictation_client/src/pages/TopPage/index.tsx
index 20ab130..1a4e435 100644
--- a/dictation_client/src/pages/TopPage/index.tsx
+++ b/dictation_client/src/pages/TopPage/index.tsx
@@ -86,6 +86,7 @@ const TopPage: React.FC = (): JSX.Element => {
                     };
                     instance.loginRedirect(loginRequest);
                   }}
+                  data-tag="signin"
                 >
                   {t(getTranslationID("topPage.label.signInButton"))}
                   <img
diff --git a/dictation_function/package-lock.json b/dictation_function/package-lock.json
index 7453688..b886c82 100644
--- a/dictation_function/package-lock.json
+++ b/dictation_function/package-lock.json
@@ -8,6 +8,8 @@
       "version": "1.0.0",
       "dependencies": {
         "@azure/functions": "^4.0.0",
+        "@azure/identity": "^3.1.3",
+        "@microsoft/microsoft-graph-client": "^3.0.5",
         "@sendgrid/mail": "^7.7.0",
         "dotenv": "^16.0.3",
         "mysql2": "^2.3.3",
@@ -38,6 +40,123 @@
         "node": ">=6.0.0"
       }
     },
+    "node_modules/@azure/abort-controller": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/@azure/abort-controller/-/abort-controller-1.1.0.tgz",
+      "integrity": "sha512-TrRLIoSQVzfAJX9H1JeFjzAoDGcoK1IYX1UImfceTZpsyYfWr09Ss1aHW1y5TrrR3iq6RZLBwJ3E24uwPhwahw==",
+      "dependencies": {
+        "tslib": "^2.2.0"
+      },
+      "engines": {
+        "node": ">=12.0.0"
+      }
+    },
+    "node_modules/@azure/core-auth": {
+      "version": "1.5.0",
+      "resolved": "https://registry.npmjs.org/@azure/core-auth/-/core-auth-1.5.0.tgz",
+      "integrity": "sha512-udzoBuYG1VBoHVohDTrvKjyzel34zt77Bhp7dQntVGGD0ehVq48owENbBG8fIgkHRNUBQH5k1r0hpoMu5L8+kw==",
+      "dependencies": {
+        "@azure/abort-controller": "^1.0.0",
+        "@azure/core-util": "^1.1.0",
+        "tslib": "^2.2.0"
+      },
+      "engines": {
+        "node": ">=14.0.0"
+      }
+    },
+    "node_modules/@azure/core-client": {
+      "version": "1.7.3",
+      "resolved": "https://registry.npmjs.org/@azure/core-client/-/core-client-1.7.3.tgz",
+      "integrity": "sha512-kleJ1iUTxcO32Y06dH9Pfi9K4U+Tlb111WXEnbt7R/ne+NLRwppZiTGJuTD5VVoxTMK5NTbEtm5t2vcdNCFe2g==",
+      "dependencies": {
+        "@azure/abort-controller": "^1.0.0",
+        "@azure/core-auth": "^1.4.0",
+        "@azure/core-rest-pipeline": "^1.9.1",
+        "@azure/core-tracing": "^1.0.0",
+        "@azure/core-util": "^1.0.0",
+        "@azure/logger": "^1.0.0",
+        "tslib": "^2.2.0"
+      },
+      "engines": {
+        "node": ">=14.0.0"
+      }
+    },
+    "node_modules/@azure/core-rest-pipeline": {
+      "version": "1.12.2",
+      "resolved": "https://registry.npmjs.org/@azure/core-rest-pipeline/-/core-rest-pipeline-1.12.2.tgz",
+      "integrity": "sha512-wLLJQdL4v1yoqYtEtjKNjf8pJ/G/BqVomAWxcKOR1KbZJyCEnCv04yks7Y1NhJ3JzxbDs307W67uX0JzklFdCg==",
+      "dependencies": {
+        "@azure/abort-controller": "^1.0.0",
+        "@azure/core-auth": "^1.4.0",
+        "@azure/core-tracing": "^1.0.1",
+        "@azure/core-util": "^1.3.0",
+        "@azure/logger": "^1.0.0",
+        "form-data": "^4.0.0",
+        "http-proxy-agent": "^5.0.0",
+        "https-proxy-agent": "^5.0.0",
+        "tslib": "^2.2.0"
+      },
+      "engines": {
+        "node": ">=16.0.0"
+      }
+    },
+    "node_modules/@azure/core-rest-pipeline/node_modules/@tootallnate/once": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/@tootallnate/once/-/once-2.0.0.tgz",
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+        "node": ">=10"
+      }
+    },
+    "node_modules/jsonwebtoken/node_modules/semver": {
+      "version": "7.5.4",
+      "resolved": "https://registry.npmjs.org/semver/-/semver-7.5.4.tgz",
+      "integrity": "sha512-1bCSESV6Pv+i21Hvpxp3Dx+pSD8lIPt8uVjRrxAUt/nbswYc+tK6Y2btiULjd4+fnq15PX+nqQDC7Oft7WkwcA==",
+      "dependencies": {
+        "lru-cache": "^6.0.0"
+      },
+      "bin": {
+        "semver": "bin/semver.js"
+      },
+      "engines": {
+        "node": ">=10"
+      }
+    },
+    "node_modules/jwa": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/jwa/-/jwa-2.0.0.tgz",
+      "integrity": "sha512-jrZ2Qx916EA+fq9cEAeCROWPTfCwi1IVHqT2tapuqLEVVDKFDENFw1oL+MwrTvH6msKxsd1YTDVw6uKEcsrLEA==",
+      "dependencies": {
+        "buffer-equal-constant-time": "1.0.1",
+        "ecdsa-sig-formatter": "1.0.11",
+        "safe-buffer": "^5.0.1"
+      }
+    },
+    "node_modules/jws": {
+      "version": "4.0.0",
+      "resolved": "https://registry.npmjs.org/jws/-/jws-4.0.0.tgz",
+      "integrity": "sha512-KDncfTmOZoOMTFG4mBlG0qUIOlc03fmzH+ru6RgYVZhPkyiy/92Owlt/8UEN+a4TXR1FQetfIpJE8ApdvdVxTg==",
+      "dependencies": {
+        "jwa": "^2.0.0",
+        "safe-buffer": "^5.0.1"
+      }
+    },
     "node_modules/kleur": {
       "version": "3.0.3",
       "resolved": "https://registry.npmjs.org/kleur/-/kleur-3.0.3.tgz",
@@ -4783,12 +5191,61 @@
         "node": ">=8"
       }
     },
+    "node_modules/lodash.defaults": {
+      "version": "4.2.0",
+      "resolved": "https://registry.npmjs.org/lodash.defaults/-/lodash.defaults-4.2.0.tgz",
+      "integrity": "sha512-qjxPLHd3r5DnsdGacqOMU6pb/avJzdh9tFX2ymgoZE27BmjXrNy/y4LoaiTeAb+O3gL8AfpJGtqfX/ae2leYYQ==",
+      "optional": true,
+      "peer": true
+    },
+    "node_modules/lodash.includes": {
+      "version": "4.3.0",
+      "resolved": "https://registry.npmjs.org/lodash.includes/-/lodash.includes-4.3.0.tgz",
+      "integrity": "sha512-W3Bx6mdkRTGtlJISOvVD/lbqjTlPPUDTMnlXZFnVwi9NKJ6tiAk6LVdlhZMm17VZisqhKcgzpO5Wz91PCt5b0w=="
+    },
+    "node_modules/lodash.isarguments": {
+      "version": "3.1.0",
+      "resolved": "https://registry.npmjs.org/lodash.isarguments/-/lodash.isarguments-3.1.0.tgz",
+      "integrity": "sha512-chi4NHZlZqZD18a0imDHnZPrDeBbTtVN7GXMwuGdRH9qotxAjYs3aVLKc7zNOG9eddR5Ksd8rvFEBc9SsggPpg==",
+      "optional": true,
+      "peer": true
+    },
+    "node_modules/lodash.isboolean": {
+      "version": "3.0.3",
+      "resolved": "https://registry.npmjs.org/lodash.isboolean/-/lodash.isboolean-3.0.3.tgz",
+      "integrity": "sha512-Bz5mupy2SVbPHURB98VAcw+aHh4vRV5IPNhILUCsOzRmsTmSQ17jIuqopAentWoehktxGd9e/hbIXq980/1QJg=="
+    },
+    "node_modules/lodash.isinteger": {
+      "version": "4.0.4",
+      "resolved": "https://registry.npmjs.org/lodash.isinteger/-/lodash.isinteger-4.0.4.tgz",
+      "integrity": "sha512-DBwtEWN2caHQ9/imiNeEA5ys1JoRtRfY3d7V9wkqtbycnAmTvRRmbHKDV4a0EYc678/dia0jrte4tjYwVBaZUA=="
+    },
+    "node_modules/lodash.isnumber": {
+      "version": "3.0.3",
+      "resolved": "https://registry.npmjs.org/lodash.isnumber/-/lodash.isnumber-3.0.3.tgz",
+      "integrity": "sha512-QYqzpfwO3/CWf3XP+Z+tkQsfaLL/EnUlXWVkIk5FUPc4sBdTehEqZONuyRt2P67PXAk+NXmTBcc97zw9t1FQrw=="
+    },
+    "node_modules/lodash.isplainobject": {
+      "version": "4.0.6",
+      "resolved": "https://registry.npmjs.org/lodash.isplainobject/-/lodash.isplainobject-4.0.6.tgz",
+      "integrity": "sha512-oSXzaWypCMHkPC3NvBEaPHf0KsA5mvPrOPgQWDsbg8n7orZ290M0BmC/jgRZ4vcJ6DTAhjrsSYgdsW/F+MFOBA=="
+    },
+    "node_modules/lodash.isstring": {
+      "version": "4.0.1",
+      "resolved": "https://registry.npmjs.org/lodash.isstring/-/lodash.isstring-4.0.1.tgz",
+      "integrity": "sha512-0wJxfxH1wgO3GrbuP+dTTk7op+6L41QCXbGINEmD+ny/G/eCqGzxyCsh7159S+mgDDcoarnBw6PC1PS5+wUGgw=="
+    },
     "node_modules/lodash.memoize": {
       "version": "4.1.2",
       "resolved": "https://registry.npmjs.org/lodash.memoize/-/lodash.memoize-4.1.2.tgz",
       "integrity": "sha512-t7j+NzmgnQzTAYXcsHYLgimltOV1MXHtlOWf6GjL9Kj8GK5FInw5JotxvbOs+IvV1/Dzo04/fCGfLVs7aXb4Ag==",
       "dev": true
     },
+    "node_modules/lodash.once": {
+      "version": "4.1.1",
+      "resolved": "https://registry.npmjs.org/lodash.once/-/lodash.once-4.1.1.tgz",
+      "integrity": "sha512-Sb487aTOCr9drQVL8pIxOzVhafOjZN9UU54hiN8PU3uAiSV7lx1yYNpbNmex2PK6dSJoNTSJUUswT651yww3Mg=="
+    },
     "node_modules/long": {
       "version": "4.0.0",
       "resolved": "https://registry.npmjs.org/long/-/long-4.0.0.tgz",
@@ -4958,7 +5415,6 @@
       "version": "1.52.0",
       "resolved": "https://registry.npmjs.org/mime-db/-/mime-db-1.52.0.tgz",
       "integrity": "sha512-sPU4uV7dYlvtWJxwwxHD0PuihVNiE7TyAbQ5SWxDCB9mUYvOgroQOwYQQOKPJ8CIbE+1ETVlOoK1UC2nU3gYvg==",
-      "dev": true,
       "engines": {
         "node": ">= 0.6"
       }
@@ -4967,7 +5423,6 @@
       "version": "2.1.35",
       "resolved": "https://registry.npmjs.org/mime-types/-/mime-types-2.1.35.tgz",
       "integrity": "sha512-ZDY+bPm5zTTF+YpCrAU9nK0UgICYPT0QtT1NZWFv4s++TNkcgVaT0g6+4R2uI4MjQjzysHB1zxuWL50hzaeXiw==",
-      "dev": true,
       "dependencies": {
         "mime-db": "1.52.0"
       },
@@ -5601,6 +6056,22 @@
         "url": "https://github.com/sponsors/sindresorhus"
       }
     },
+    "node_modules/open": {
+      "version": "8.4.2",
+      "resolved": "https://registry.npmjs.org/open/-/open-8.4.2.tgz",
+      "integrity": "sha512-7x81NCL719oNbsq/3mh+hVrAWmFuEYUqrq/Iw3kUzH8ReypT9QQ0BLoJS7/G9k6N81XjW4qHWtjWwe/9eLy1EQ==",
+      "dependencies": {
+        "define-lazy-prop": "^2.0.0",
+        "is-docker": "^2.1.1",
+        "is-wsl": "^2.2.0"
+      },
+      "engines": {
+        "node": ">=12"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
     "node_modules/p-limit": {
       "version": "3.1.0",
       "resolved": "https://registry.npmjs.org/p-limit/-/p-limit-3.1.0.tgz",
@@ -5896,6 +6367,66 @@
         "node": ">= 6"
       }
     },
+    "node_modules/redis": {
+      "version": "3.1.2",
+      "resolved": "https://registry.npmjs.org/redis/-/redis-3.1.2.tgz",
+      "integrity": "sha512-grn5KoZLr/qrRQVwoSkmzdbw6pwF+/rwODtrOr6vuBRiR/f3rjSTGupbF90Zpqm2oenix8Do6RV7pYEkGwlKkw==",
+      "optional": true,
+      "peer": true,
+      "dependencies": {
+        "denque": "^1.5.0",
+        "redis-commands": "^1.7.0",
+        "redis-errors": "^1.2.0",
+        "redis-parser": "^3.0.0"
+      },
+      "engines": {
+        "node": ">=10"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/node-redis"
+      }
+    },
+    "node_modules/redis-commands": {
+      "version": "1.7.0",
+      "resolved": "https://registry.npmjs.org/redis-commands/-/redis-commands-1.7.0.tgz",
+      "integrity": "sha512-nJWqw3bTFy21hX/CPKHth6sfhZbdiHP6bTawSgQBlKOVRG7EZkfHbbHwQJnrE4vsQf0CMNE+3gJ4Fmm16vdVlQ==",
+      "optional": true,
+      "peer": true
+    },
+    "node_modules/redis-errors": {
+      "version": "1.2.0",
+      "resolved": "https://registry.npmjs.org/redis-errors/-/redis-errors-1.2.0.tgz",
+      "integrity": "sha512-1qny3OExCf0UvUV/5wpYKf2YwPcOqXzkwKKSmKHiE6ZMQs5heeE/c8eXK+PNllPvmjgAbfnsbpkGZWy8cBpn9w==",
+      "optional": true,
+      "peer": true,
+      "engines": {
+        "node": ">=4"
+      }
+    },
+    "node_modules/redis-parser": {
+      "version": "3.0.0",
+      "resolved": "https://registry.npmjs.org/redis-parser/-/redis-parser-3.0.0.tgz",
+      "integrity": "sha512-DJnGAeenTdpMEH6uAJRK/uiyEIH9WVsUmoLwzudwGJUwZPp80PDBWPHXSAGNPwNvIXAbe7MSUB1zQFugFml66A==",
+      "optional": true,
+      "peer": true,
+      "dependencies": {
+        "redis-errors": "^1.0.0"
+      },
+      "engines": {
+        "node": ">=4"
+      }
+    },
+    "node_modules/redis/node_modules/denque": {
+      "version": "1.5.1",
+      "resolved": "https://registry.npmjs.org/denque/-/denque-1.5.1.tgz",
+      "integrity": "sha512-XwE+iZ4D6ZUB7mfYRMb5wByE8L74HCn30FBN7sWnXksWc1LO1bPDl67pBR9o/kC4z/xSNAwkMYcGgqDV3BE3Hw==",
+      "optional": true,
+      "peer": true,
+      "engines": {
+        "node": ">=0.10"
+      }
+    },
     "node_modules/reflect-metadata": {
       "version": "0.1.13",
       "resolved": "https://registry.npmjs.org/reflect-metadata/-/reflect-metadata-0.1.13.tgz",
@@ -6123,8 +6654,13 @@
       "resolved": "https://registry.npmjs.org/slash/-/slash-3.0.0.tgz",
       "integrity": "sha512-g9Q1haeby36OSStwb4ntCGGGaKsaVSjQ68fBxoQcutl5fS1vuY18H3wSt3jFyFtrkx+Kz0V1G85A4MyAdDMi2Q==",
       "dev": true,
+      "dependencies": {
+        "@babel/helper-validator-identifier": "^7.22.20",
+        "chalk": "^2.4.2",
+        "js-tokens": "^4.0.0"
+      },
       "engines": {
-        "node": ">=8"
+        "node": ">=6.9.0"
       }
     },
     "node_modules/smart-buffer": {
@@ -6262,6 +6798,22 @@
         "node": ">=10"
       }
     },
+    "node_modules/standard-as-callback": {
+      "version": "2.1.0",
+      "resolved": "https://registry.npmjs.org/standard-as-callback/-/standard-as-callback-2.1.0.tgz",
+      "integrity": "sha512-qoRRSyROncaz1z0mvYqIE4lCd9p2R90i6GxW3uZv5ucSu8tU7B5HXUP1gG8pVZsYNVaXjk8ClXHPttLyxAL48A==",
+      "optional": true,
+      "peer": true
+    },
+    "node_modules/stoppable": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/stoppable/-/stoppable-1.1.0.tgz",
+      "integrity": "sha512-KXDYZ9dszj6bzvnEMRYvxgeTHU74QBFL54XKtP3nyMuJ81CFYtABZ3bAzL2EdFUaEwJOBOgENyFj3R7oTzDyyw==",
+      "engines": {
+        "node": ">=4",
+        "npm": ">=6"
+      }
+    },
     "node_modules/string_decoder": {
       "version": "1.3.0",
       "resolved": "https://registry.npmjs.org/string_decoder/-/string_decoder-1.3.0.tgz",
@@ -6388,8 +6940,8 @@
       "dependencies": {
         "ansi-regex": "^5.0.1"
       },
-      "engines": {
-        "node": ">=8"
+      "peerDependencies": {
+        "@babel/core": "^7.0.0-0"
       }
     },
     "node_modules/strip-ansi-cjs/node_modules/ansi-regex": {
diff --git a/dictation_function/package.json b/dictation_function/package.json
index 7f208f9..02589f6 100644
--- a/dictation_function/package.json
+++ b/dictation_function/package.json
@@ -13,6 +13,8 @@
   },
   "dependencies": {
     "@azure/functions": "^4.0.0",
+    "@azure/identity": "^3.1.3",
+    "@microsoft/microsoft-graph-client": "^3.0.5",
     "@sendgrid/mail": "^7.7.0",
     "dotenv": "^16.0.3",
     "mysql2": "^2.3.3",
diff --git a/dictation_function/src/adb2c/adb2c.service.ts b/dictation_function/src/adb2c/adb2c.service.ts
new file mode 100644
index 0000000..8caa96c
--- /dev/null
+++ b/dictation_function/src/adb2c/adb2c.service.ts
@@ -0,0 +1,74 @@
+import { ClientSecretCredential } from "@azure/identity";
+import { Client } from "@microsoft/microsoft-graph-client";
+import { TokenCredentialAuthenticationProvider } from "@microsoft/microsoft-graph-client/authProviders/azureTokenCredentials";
+import { AdB2cResponse, AdB2cUser } from "./types/types";
+import { error } from "console";
+
+export class Adb2cTooManyRequestsError extends Error {}
+
+export class AdB2cService {
+  private graphClient: Client;
+
+  constructor() {
+    // ADB2Cへの認証情報
+    if (
+      !process.env.ADB2C_TENANT_ID ||
+      !process.env.ADB2C_CLIENT_ID ||
+      !process.env.ADB2C_CLIENT_SECRET
+    ) {
+      throw error;
+    }
+    const credential = new ClientSecretCredential(
+      process.env.ADB2C_TENANT_ID,
+      process.env.ADB2C_CLIENT_ID,
+      process.env.ADB2C_CLIENT_SECRET
+    );
+    const authProvider = new TokenCredentialAuthenticationProvider(credential, {
+      scopes: ["https://graph.microsoft.com/.default"],
+    });
+
+    this.graphClient = Client.initWithMiddleware({ authProvider });
+  }
+
+  /**
+   * Azure AD B2Cからユーザ情報を取得する
+   * @param externalIds 外部ユーザーID
+   * @returns ユーザ情報
+   */
+  async getUsers(externalIds: string[]): Promise<AdB2cUser[]> {
+    const chunkExternalIds = splitArrayInChunksOfFifteen(externalIds);
+
+    try {
+      const b2cUsers: AdB2cUser[] = [];
+      for (let index = 0; index < chunkExternalIds.length; index++) {
+        const element = chunkExternalIds[index];
+        const res: AdB2cResponse = await this.graphClient
+          .api(`users/`)
+          .select(["id", "displayName", "identities"])
+          .filter(`id in (${element.map((y) => `'${y}'`).join(",")})`)
+          .get();
+
+        b2cUsers.push(...res.value);
+      }
+
+      return b2cUsers;
+    } catch (e) {
+      const { statusCode } = e;
+      if (statusCode === 429) {
+        throw new Adb2cTooManyRequestsError();
+      }
+
+      throw e;
+    } finally {
+    }
+  }
+}
+
+const splitArrayInChunksOfFifteen = (arr: string[]): string[][] => {
+  const result: string[][] = [];
+  const chunkSize = 15; // SDKの制限数
+  for (let i = 0; i < arr.length; i += chunkSize) {
+    result.push(arr.slice(i, i + chunkSize));
+  }
+  return result;
+};
diff --git a/dictation_function/src/adb2c/types/types.ts b/dictation_function/src/adb2c/types/types.ts
new file mode 100644
index 0000000..a7261ef
--- /dev/null
+++ b/dictation_function/src/adb2c/types/types.ts
@@ -0,0 +1,15 @@
+export type AdB2cResponse = {
+  '@odata.context': string;
+  value: AdB2cUser[];
+};
+export type AdB2cUser = {
+  id: string;
+  displayName: string;
+  identities?: UserIdentity[];
+};
+
+export type UserIdentity = {
+  signInType: string;
+  issuer: string;
+  issuerAssignedId: string;
+};
diff --git a/dictation_function/src/common/cache/constants.ts b/dictation_function/src/common/cache/constants.ts
new file mode 100644
index 0000000..da6c13e
--- /dev/null
+++ b/dictation_function/src/common/cache/constants.ts
@@ -0,0 +1 @@
+export const ADB2C_PREFIX = "adb2c-external-id:"
\ No newline at end of file
diff --git a/dictation_function/src/common/cache/index.ts b/dictation_function/src/common/cache/index.ts
new file mode 100644
index 0000000..067be25
--- /dev/null
+++ b/dictation_function/src/common/cache/index.ts
@@ -0,0 +1,19 @@
+import { ADB2C_PREFIX } from './constants';
+
+/**
+ * ADB2Cのユーザー格納用のキーを生成する
+ * @param externalId 外部ユーザーID
+ * @returns キャッシュのキー
+ */
+export const makeADB2CKey = (externalId: string): string => {
+	return `${ADB2C_PREFIX}${externalId}`;
+}
+
+/**
+ * ADB2Cのユーザー格納用のキーから外部ユーザーIDを取得する
+ * @param key キャッシュのキー
+ * @returns 外部ユーザーID
+ */
+export const restoreAdB2cID = (key: string): string => {
+	return key.replace(ADB2C_PREFIX, '');
+}
\ No newline at end of file
diff --git a/dictation_function/src/common/getEnv/getEnv.ts b/dictation_function/src/common/getEnv/getEnv.ts
new file mode 100644
index 0000000..7a8a738
--- /dev/null
+++ b/dictation_function/src/common/getEnv/getEnv.ts
@@ -0,0 +1,7 @@
+export const getMailFrom = (): string => {
+  const from = process.env.MAIL_FROM;
+  if (typeof from === "string") {
+    return from;
+  }
+  throw new Error("MAIL_FROM not found");
+};
diff --git a/dictation_function/src/common/test/utility.ts b/dictation_function/src/common/test/utility.ts
deleted file mode 100644
index 768eec5..0000000
--- a/dictation_function/src/common/test/utility.ts
+++ /dev/null
@@ -1,71 +0,0 @@
-import { v4 as uuidv4 } from "uuid";
-import { DataSource } from "typeorm";
-import { User } from "../../entity/user.entity";
-import { Account } from "../../entity/account.entity";
-import { ADMIN_ROLES, USER_ROLES } from "../../constants";
-
-type InitialTestDBState = {
-  tier1Accounts: { account: Account; users: User[] }[];
-  tier2Accounts: { account: Account; users: User[] }[];
-  tier3Accounts: { account: Account; users: User[] }[];
-  tier4Accounts: { account: Account; users: User[] }[];
-  tier5Accounts: { account: Account; users: User[] }[];
-};
-
-// 上書きされたら困る項目を除外したAccount型
-type OverrideAccount = Omit<
-  Account,
-  "id" | "primary_admin_user_id" | "secondary_admin_user_id" | "user"
->;
-
-// 上書きされたら困る項目を除外したUser型
-type OverrideUser = Omit<
-  User,
-  "id" | "account" | "license" | "userGroupMembers"
->;
-
-type AccountDefault = { [K in keyof OverrideAccount]?: OverrideAccount[K] };
-type UserDefault = { [K in keyof OverrideUser]?: OverrideUser[K] };
-
-/**
- * テスト ユーティリティ: 指定したプロパティを上書きしたユーザーを作成する
- * @param dataSource データソース
- * @param defaultUserValue User型と同等かつoptionalなプロパティを持つ上書き箇所指定用オブジェクト
- * @returns 作成したユーザー
- */
-export const makeTestUser = async (
-  datasource: DataSource,
-  defaultUserValue?: UserDefault
-): Promise<User> => {
-  const d = defaultUserValue;
-  const { identifiers } = await datasource.getRepository(User).insert({
-    account_id: d?.account_id ?? -1,
-    external_id: d?.external_id ?? uuidv4(),
-    role: d?.role ?? `${ADMIN_ROLES.STANDARD} ${USER_ROLES.NONE}`,
-    author_id: d?.author_id,
-    accepted_eula_version: d?.accepted_eula_version ?? "1.0",
-    accepted_dpa_version: d?.accepted_dpa_version ?? "1.0",
-    email_verified: d?.email_verified ?? true,
-    auto_renew: d?.auto_renew ?? true,
-    license_alert: d?.license_alert ?? true,
-    notification: d?.notification ?? true,
-    encryption: d?.encryption ?? true,
-    encryption_password: d?.encryption_password,
-    prompt: d?.prompt ?? true,
-    created_by: d?.created_by ?? "test_runner",
-    created_at: d?.created_at ?? new Date(),
-    updated_by: d?.updated_by ?? "updater",
-    updated_at: d?.updated_at ?? new Date(),
-  });
-  const result = identifiers.pop() as User;
-
-  const user = await datasource.getRepository(User).findOne({
-    where: {
-      id: result.id,
-    },
-  });
-  if (!user) {
-    throw new Error("Unexpected null");
-  }
-  return user;
-};
diff --git a/dictation_function/src/common/types/types.ts b/dictation_function/src/common/types/types.ts
new file mode 100644
index 0000000..88ff9a4
--- /dev/null
+++ b/dictation_function/src/common/types/types.ts
@@ -0,0 +1,70 @@
+import {
+  LICENSE_EXPIRATION_DAYS,
+  LICENSE_EXPIRATION_THRESHOLD_DAYS,
+  TRIAL_LICENSE_EXPIRATION_DAYS,
+} from "../../constants";
+
+// ライセンス算出用に、その日の始まりの時刻（0:00:00.000）の日付を取得する
+export class DateWithZeroTime extends Date {
+  constructor(...args: any[]) {
+    if (args.length === 0) {
+      super(); // 引数がない場合、現在の日付で初期化
+    } else {
+      super(...(args as [string])); // 引数がある場合、引数をそのままDateクラスのコンストラクタに渡す
+    }
+    this.setHours(0, 0, 0, 0); // 時分秒を"0:00:00.000"に固定
+  }
+}
+
+// ライセンス算出用に、その日の終わりの時刻（23:59:59.999）の日付を取得する
+export class DateWithDayEndTime extends Date {
+  constructor(...args: any[]) {
+    if (args.length === 0) {
+      super(); // 引数がない場合、現在の日付で初期化
+    } else {
+      super(...(args as [string])); // 引数がある場合、引数をそのままDateクラスのコンストラクタに渡す
+    }
+    this.setHours(23, 59, 59, 999); // 時分秒を"23:59:59.999"に固定
+  }
+}
+
+// ライセンスの算出用に、閾値となる時刻（23:59:59.999）の日付を取得する
+export class ExpirationThresholdDate extends Date {
+  constructor(...args: any[]) {
+    if (args.length === 0) {
+      super(); // 引数がない場合、現在の日付で初期化
+    } else {
+      super(...(args as [string])); // 引数がある場合、引数をそのままDateクラスのコンストラクタに渡す
+    }
+    this.setDate(this.getDate() + LICENSE_EXPIRATION_THRESHOLD_DAYS);
+    this.setHours(23, 59, 59, 999); // 時分秒を"23:59:59.999"に固定
+  }
+}
+
+// 新規トライアルライセンス発行時の有効期限算出用に、30日後の日付を取得する
+export class NewTrialLicenseExpirationDate extends Date {
+  constructor(...args: any[]) {
+    if (args.length === 0) {
+      super(); // 引数がない場合、現在の日付で初期化
+    } else {
+      super(...(args as [string])); // 引数がある場合、引数をそのままDateクラスのコンストラクタに渡す
+    }
+    this.setDate(this.getDate() + TRIAL_LICENSE_EXPIRATION_DAYS);
+    this.setHours(23, 59, 59); // 時分秒を"23:59:59"に固定
+    this.setMilliseconds(0);
+  }
+}
+
+// 新規ライセンス割り当て時の有効期限算出用に、365日後の日付を取得する
+export class NewAllocatedLicenseExpirationDate extends Date {
+  constructor(...args: any[]) {
+    if (args.length === 0) {
+      super(); // 引数がない場合、現在の日付で初期化
+    } else {
+      super(...(args as [string])); // 引数がある場合、引数をそのままDateクラスのコンストラクタに渡す
+    }
+    this.setDate(this.getDate() + LICENSE_EXPIRATION_DAYS);
+    this.setHours(23, 59, 59); // 時分秒を"23:59:59"に固定
+    this.setMilliseconds(0);
+  }
+}
diff --git a/dictation_function/src/entity/account.entity.ts b/dictation_function/src/entity/account.entity.ts
index 2463d5e..a8fa438 100644
--- a/dictation_function/src/entity/account.entity.ts
+++ b/dictation_function/src/entity/account.entity.ts
@@ -6,7 +6,8 @@ import {
   PrimaryGeneratedColumn,
   CreateDateColumn,
   UpdateDateColumn,
-  OneToMany,
+  OneToOne,
+  JoinColumn,
 } from "typeorm";
 
 @Entity({ name: "accounts" })
@@ -65,6 +66,11 @@ export class Account {
   }) // defaultはSQLite用設定値.本番用は別途migrationで設定
   updated_at: Date;
 
-  @OneToMany(() => User, (user) => user.id)
-  user: User[] | null;
+  @OneToOne(() => User, (user) => user.id)
+  @JoinColumn({ name: "primary_admin_user_id" })
+  primaryAdminUser: User | null;
+
+  @OneToOne(() => User, (user) => user.id)
+  @JoinColumn({ name: "secondary_admin_user_id" })
+  secondaryAdminUser: User | null;
 }
diff --git a/dictation_function/src/entity/license.entity.ts b/dictation_function/src/entity/license.entity.ts
new file mode 100644
index 0000000..2f32ae3
--- /dev/null
+++ b/dictation_function/src/entity/license.entity.ts
@@ -0,0 +1,63 @@
+import {
+  Entity,
+  Column,
+  PrimaryGeneratedColumn,
+  CreateDateColumn,
+  UpdateDateColumn,
+  JoinColumn,
+  OneToOne,
+} from "typeorm";
+import { bigintTransformer } from "../common/entity";
+import { User } from "./user.entity";
+
+@Entity({ name: "licenses" })
+export class License {
+  @PrimaryGeneratedColumn()
+  id: number;
+
+  @Column({ nullable: true, type: "datetime" })
+  expiry_date: Date | null;
+
+  @Column()
+  account_id: number;
+
+  @Column()
+  type: string;
+
+  @Column()
+  status: string;
+
+  @Column({ nullable: true, type: "bigint", transformer: bigintTransformer })
+  allocated_user_id: number | null;
+
+  @Column({ nullable: true, type: "bigint", transformer: bigintTransformer })
+  order_id: number | null;
+
+  @Column({ nullable: true, type: "datetime" })
+  deleted_at: Date | null;
+
+  @Column({ nullable: true, type: "bigint", transformer: bigintTransformer })
+  delete_order_id: number | null;
+
+  @Column({ nullable: true, type: "datetime" })
+  created_by: string | null;
+
+  @CreateDateColumn({
+    default: () => "datetime('now', 'localtime')",
+    type: "datetime",
+  })
+  created_at: Date;
+
+  @Column({ nullable: true, type: "datetime" })
+  updated_by: string | null;
+
+  @UpdateDateColumn({
+    default: () => "datetime('now', 'localtime')",
+    type: "datetime",
+  })
+  updated_at: Date;
+
+  @OneToOne(() => User, (user) => user.license)
+  @JoinColumn({ name: "allocated_user_id" })
+  user: User | null;
+}
diff --git a/dictation_function/src/entity/user.entity.ts b/dictation_function/src/entity/user.entity.ts
index 9a9b26d..573a017 100644
--- a/dictation_function/src/entity/user.entity.ts
+++ b/dictation_function/src/entity/user.entity.ts
@@ -4,7 +4,9 @@ import {
   PrimaryGeneratedColumn,
   CreateDateColumn,
   UpdateDateColumn,
+  OneToOne,
 } from "typeorm";
+import { License } from "./license.entity";
 
 @Entity({ name: "users" })
 export class User {
@@ -70,4 +72,7 @@ export class User {
     type: "datetime",
   }) // defaultはSQLite用設定値.本番用は別途migrationで設定
   updated_at: Date;
+
+  @OneToOne(() => License, (license) => license.user)
+  license: License | null;
 }
diff --git a/dictation_function/src/functions/licenseAlert.ts b/dictation_function/src/functions/licenseAlert.ts
new file mode 100644
index 0000000..d5d715a
--- /dev/null
+++ b/dictation_function/src/functions/licenseAlert.ts
@@ -0,0 +1,347 @@
+import { app, InvocationContext, Timer } from "@azure/functions";
+import { Between, DataSource, In, IsNull, MoreThan, Not } from "typeorm";
+import { User } from "../entity/user.entity";
+import { Account } from "../entity/account.entity";
+import {
+  ADB2C_SIGN_IN_TYPE,
+  LICENSE_ALLOCATED_STATUS,
+  TIERS,
+} from "../constants";
+import * as dotenv from "dotenv";
+import { License } from "../entity/license.entity";
+import {
+  DateWithDayEndTime,
+  DateWithZeroTime,
+  ExpirationThresholdDate,
+} from "../common/types/types";
+import { getMailFrom } from "../common/getEnv/getEnv";
+import { AdB2cService } from "../adb2c/adb2c.service";
+import { SendGridService } from "../sendgrid/sendgrid.service";
+
+export async function licenseAlertProcessing(
+  context: InvocationContext,
+  datasource: DataSource,
+  sendgrid: SendGridService,
+  adb2c: AdB2cService
+) {
+  context.log("[IN]licenseAlertProcessing");
+  const mailFrom = getMailFrom();
+  const accountRepository = datasource.getRepository(Account);
+
+  // 第五のアカウントを取得
+  const accounts = await accountRepository.find({
+    where: {
+      tier: TIERS.TIER5,
+    },
+    relations: {
+      primaryAdminUser: true,
+      secondaryAdminUser: true,
+    },
+  });
+
+  const licenseRepository = datasource.getRepository(License);
+  const currentDate = new DateWithZeroTime();
+  const expiringSoonDate = new ExpirationThresholdDate(currentDate.getTime());
+  const currentDateWithZeroTime = new DateWithZeroTime();
+  const currentDateWithDayEndTime = new DateWithDayEndTime();
+  const sendTargetAccounts = [] as accountInfo[];
+
+  const counts = async () => {
+    for (const account of accounts) {
+      // 有効期限がしきい値より未来または未設定で、割り当て可能なライセンス数の取得を行う
+      const allocatableLicenseWithMargin = await licenseRepository.count({
+        where: [
+          {
+            account_id: account.id,
+            status: In([
+              LICENSE_ALLOCATED_STATUS.UNALLOCATED,
+              LICENSE_ALLOCATED_STATUS.REUSABLE,
+            ]),
+            expiry_date: MoreThan(expiringSoonDate),
+          },
+          {
+            account_id: account.id,
+            status: In([
+              LICENSE_ALLOCATED_STATUS.UNALLOCATED,
+              LICENSE_ALLOCATED_STATUS.REUSABLE,
+            ]),
+            expiry_date: IsNull(),
+          },
+        ],
+      });
+
+      // 有効期限が現在日付からしきい値以内のライセンス数を取得する
+      const expiringSoonLicense = await licenseRepository.count({
+        where: {
+          account_id: account.id,
+          expiry_date: Between(currentDate, expiringSoonDate),
+          status: Not(LICENSE_ALLOCATED_STATUS.DELETED),
+        },
+      });
+      // shortage算出
+      let shortage = allocatableLicenseWithMargin - expiringSoonLicense;
+      shortage = shortage >= 0 ? 0 : Math.abs(shortage);
+
+      // AutoRenewが未チェックかつ、有効期限当日のライセンスが割り当てられているユーザー数を取得
+      const userCount = await licenseRepository.count({
+        where: [
+          {
+            account_id: account.id,
+            expiry_date: Between(
+              currentDateWithZeroTime,
+              currentDateWithDayEndTime
+            ),
+            status: LICENSE_ALLOCATED_STATUS.ALLOCATED,
+            user: {
+              auto_renew: false,
+            },
+          },
+        ],
+        relations: {
+          user: true,
+        },
+      });
+
+      // 上で取得したshortageとユーザー数のどちらかが1以上ならプライマリ、セカンダリ管理者、親企業名を保持する
+      // （shortageとユーザー数のどちらかが1以上 = アラートメールを送る必要がある）
+      let primaryAdminExternalId: string | undefined;
+      let secondaryAdminExternalId: string | undefined;
+      let parentCompanyName: string | undefined;
+      if (shortage !== 0 || userCount !== 0) {
+        primaryAdminExternalId = account.primaryAdminUser
+          ? account.primaryAdminUser.external_id
+          : undefined;
+        secondaryAdminExternalId = account.secondaryAdminUser
+          ? account.secondaryAdminUser.external_id
+          : undefined;
+        // 第五のアカウントを取得
+        // strictNullChecks対応
+        if (account.parent_account_id) {
+          const parent = await accountRepository.findOne({
+            where: {
+              id: account.parent_account_id,
+            },
+          });
+          parentCompanyName = parent?.company_name;
+        }
+      } else {
+        primaryAdminExternalId = undefined;
+        secondaryAdminExternalId = undefined;
+        parentCompanyName = undefined;
+      }
+      sendTargetAccounts.push({
+        accountId: account.id,
+        companyName: account.company_name,
+        parentCompanyName: parentCompanyName,
+        shortage: shortage,
+        userCountOfLicenseExpiringSoon: userCount,
+        primaryAdminExternalId: primaryAdminExternalId,
+        secondaryAdminExternalId: secondaryAdminExternalId,
+        primaryAdminEmail: undefined,
+        secondaryAdminEmail: undefined,
+      });
+    }
+  };
+  await counts();
+
+  // ADB2Cからユーザーを取得する用の外部ID配列を作成
+  const externalIds = [] as string[];
+  sendTargetAccounts.map((x) => {
+    if (x.primaryAdminExternalId) {
+      externalIds.push(x.primaryAdminExternalId);
+    }
+    if (x.secondaryAdminExternalId) {
+      externalIds.push(x.secondaryAdminExternalId);
+    }
+  });
+  const adb2cUsers = await adb2c.getUsers(externalIds);
+
+  // ADB2Cから取得したメールアドレスをRDBから取得した情報にマージ
+  sendTargetAccounts.map((info) => {
+    const primaryAdminUser = adb2cUsers.find(
+      (adb2c) => info.primaryAdminExternalId === adb2c.id
+    );
+    if (primaryAdminUser) {
+      const primaryAdminMail = primaryAdminUser.identities?.find(
+        (identity) => identity.signInType === ADB2C_SIGN_IN_TYPE.EMAILADDRESS
+      )?.issuerAssignedId;
+      if (primaryAdminMail) {
+        info.primaryAdminEmail = primaryAdminMail;
+      }
+
+      const secondaryAdminUser = adb2cUsers.find(
+        (adb2c) => info.secondaryAdminExternalId === adb2c.id
+      );
+      if (secondaryAdminUser) {
+        const secondaryAdminMail = secondaryAdminUser.identities?.find(
+          (identity) => identity.signInType === ADB2C_SIGN_IN_TYPE.EMAILADDRESS
+        )?.issuerAssignedId;
+        if (secondaryAdminMail) {
+          info.secondaryAdminEmail = secondaryAdminMail;
+        }
+      }
+    }
+  });
+
+  const sendMail = async () => {
+    for (const targetAccount of sendTargetAccounts) {
+      // プライマリ管理者が入っているかチェック
+      // 入っていない場合は、アラートメールを送信する必要が無いため、何も処理をせず次のループへ
+      if (targetAccount.primaryAdminExternalId) {
+        // メール送信
+        // strictNullChecks対応
+        if (targetAccount.primaryAdminEmail) {
+          // ライセンス不足メール
+          if (targetAccount.shortage !== 0) {
+            const { subject, text, html } =
+              await sendgrid.createMailContentOfLicenseShortage();
+            // メールを送信
+            try {
+              await sendgrid.sendMail(
+                targetAccount.primaryAdminEmail,
+                mailFrom,
+                subject,
+                text,
+                html
+              );
+              context.log(
+                `Shortage mail send success. mail to :${targetAccount.primaryAdminEmail}`
+              );
+            } catch {
+              context.log(
+                `Shortage mail send failed. mail to :${targetAccount.primaryAdminEmail}`
+              );
+            }
+
+            // セカンダリ管理者が存在する場合、セカンダリ管理者にも送信
+            if (targetAccount.secondaryAdminEmail) {
+              // ライセンス不足メール
+              if (targetAccount.shortage !== 0) {
+                const { subject, text, html } =
+                  await sendgrid.createMailContentOfLicenseShortage();
+                // メールを送信
+                try {
+                  await sendgrid.sendMail(
+                    targetAccount.secondaryAdminEmail,
+                    mailFrom,
+                    subject,
+                    text,
+                    html
+                  );
+                  context.log(
+                    `Shortage mail send success. mail to :${targetAccount.secondaryAdminEmail}`
+                  );
+                } catch {
+                  context.log(
+                    `Shortage mail send failed. mail to :${targetAccount.secondaryAdminEmail}`
+                  );
+                }
+              }
+            }
+          }
+
+          // ライセンス失効警告メール
+          if (targetAccount.userCountOfLicenseExpiringSoon !== 0) {
+            const { subject, text, html } =
+              await sendgrid.createMailContentOfLicenseExpiringSoon();
+            // メールを送信
+            try {
+              await sendgrid.sendMail(
+                targetAccount.primaryAdminEmail,
+                mailFrom,
+                subject,
+                text,
+                html
+              );
+              context.log(
+                `Expiring soon mail send success. mail to :${targetAccount.primaryAdminEmail}`
+              );
+            } catch {
+              context.log(
+                `Expiring soon mail send failed. mail to :${targetAccount.primaryAdminEmail}`
+              );
+            }
+
+            // セカンダリ管理者が存在する場合、セカンダリ管理者にも送信
+            if (targetAccount.secondaryAdminEmail) {
+              // ライセンス不足メール
+              if (targetAccount.shortage !== 0) {
+                const { subject, text, html } =
+                  await sendgrid.createMailContentOfLicenseExpiringSoon();
+                // メールを送信
+                try {
+                  await sendgrid.sendMail(
+                    targetAccount.secondaryAdminEmail,
+                    mailFrom,
+                    subject,
+                    text,
+                    html
+                  );
+                  context.log(
+                    `Expiring soon mail send success. mail to :${targetAccount.secondaryAdminEmail}`
+                  );
+                } catch {
+                  context.log(
+                    `Expiring soon mail send failed. mail to :${targetAccount.secondaryAdminEmail}`
+                  );
+                }
+              }
+            }
+          }
+        }
+      }
+    }
+  };
+  await sendMail();
+
+  context.log("[OUT]licenseAlertProcessing");
+}
+
+export async function licenseAlert(
+  myTimer: Timer,
+  context: InvocationContext
+): Promise<void> {
+  context.log("[IN]licenseAlert");
+
+  dotenv.config({ path: ".env" });
+  dotenv.config({ path: ".env.local", override: true });
+  const datasource = new DataSource({
+    type: "mysql",
+    host: process.env.DB_HOST,
+    port: Number(process.env.DB_PORT),
+    username: process.env.DB_USERNAME,
+    password: process.env.DB_PASSWORD,
+    database: process.env.DB_NAME,
+    entities: [User, Account, License],
+  });
+  await datasource.initialize();
+
+  const adb2c = new AdB2cService();
+  const sendgrid = new SendGridService();
+  try {
+    await licenseAlertProcessing(context, datasource, sendgrid, adb2c);
+  } catch (e) {
+    context.log("licenseAlertProcessing failed");
+    context.error(e);
+  } finally {
+    await datasource.destroy();
+    context.log("[OUT]licenseAlert");
+  }
+}
+
+app.timer("licenseAlert", {
+  schedule: "0 */1 * * * *",
+  handler: licenseAlert,
+});
+
+class accountInfo {
+  accountId: number;
+  companyName: string;
+  parentCompanyName: string | undefined;
+  shortage: number;
+  userCountOfLicenseExpiringSoon: number;
+  primaryAdminExternalId: string | undefined;
+  secondaryAdminExternalId: string | undefined;
+  primaryAdminEmail: string | undefined;
+  secondaryAdminEmail: string | undefined;
+}
diff --git a/dictation_function/src/functions/timerTriggerExample.ts b/dictation_function/src/functions/timerTriggerExample.ts
deleted file mode 100644
index 8374607..0000000
--- a/dictation_function/src/functions/timerTriggerExample.ts
+++ /dev/null
@@ -1,70 +0,0 @@
-import { app, InvocationContext, Timer } from "@azure/functions";
-import { DataSource } from "typeorm";
-import { User } from "../entity/user.entity";
-import { SendGridService } from "../sendgrid/sendgrid.service";
-import * as dotenv from "dotenv";
-
-// タイマートリガー処理のサンプルです
-// TODO:開発が進んだら削除すること
-export async function timerTriggerExample(
-  myTimer: Timer,
-  context: InvocationContext
-): Promise<void> {
-  context.log("Timer function processed request.");
-
-  dotenv.config({ path: ".env" });
-  const datasource = new DataSource({
-    type: "mysql",
-    host: process.env.DB_HOST,
-    port: Number(process.env.DB_PORT),
-    username: process.env.DB_USERNAME,
-    password: process.env.DB_PASSWORD,
-    database: process.env.DB_NAME,
-    entities: [User],
-  });
-
-  try {
-    await datasource.initialize();
-    const userRepository = datasource.getRepository(User); // Userエンティティに対応するリポジトリを取得
-
-    // ユーザーを検索
-    const users = await userRepository.find();
-    console.log(users);
-  } catch (e) {
-    console.error(e);
-  } finally {
-    await datasource.destroy();
-  }
-}
-
-// test実行確認用サンプル
-// TODO:開発が進んだら削除すること
-export async function testExample(datasource: DataSource): Promise<User[]> {
-  let users: User[];
-  const userRepository = datasource.getRepository(User); // Userエンティティに対応するリポジトリを取得
-
-  // ユーザーを検索
-  users = await userRepository.find();
-  return users;
-}
-
-// test実行確認用サンプル
-// TODO:開発が進んだら削除すること
-export async function testSendgridExample(): Promise<string> {
-  const sendgrid = new SendGridService();
-
-  // メールを送信
-  await sendgrid.sendMail(
-    "oura.a89@gmail.com",
-    process.env.MAIL_FROM,
-    "testMail",
-    "test!",
-    "html"
-  );
-  return "sucsess";
-}
-
-app.timer("timerTriggerExample", {
-  schedule: "0 */1 * * * *",
-  handler: timerTriggerExample,
-});
diff --git a/dictation_function/src/sendgrid/sendgrid.service.ts b/dictation_function/src/sendgrid/sendgrid.service.ts
index a5bed4c..2fd9a7a 100644
--- a/dictation_function/src/sendgrid/sendgrid.service.ts
+++ b/dictation_function/src/sendgrid/sendgrid.service.ts
@@ -1,25 +1,48 @@
 import sendgrid from "@sendgrid/mail";
+import { error } from "console";
 
 export class SendGridService {
   constructor() {
+    if (!process.env.SENDGRID_API_KEY) {
+      throw error;
+    }
     sendgrid.setApiKey(process.env.SENDGRID_API_KEY);
   }
   /**
-   * メールコンテンツを作成する
+   * メールコンテンツを作成する(ライセンス不足)
    * @param accountId 認証対象のユーザーが所属するアカウントのID
    * @param userId 認証対象のユーザーのID
    * @param email  認証対象のユーザーのメールアドレス
    * @returns メールのサブジェクトとコンテンツ
    */
-  async createMailContent(
-    accountId: number,
-    userId: number,
-    email: string
-  ): Promise<{ subject: string; text: string; html: string }> {
+  async createMailContentOfLicenseShortage(): Promise<{
+    subject: string;
+    text: string;
+    html: string;
+  }> {
     return {
-      subject: "Verify your new account",
-      text: `The verification URL.`,
-      html: `<p>The verification URL.<p>`,
+      subject: "ライセンス在庫不足通知",
+      text: `ライセンス在庫不足通知：本文`,
+      html: `<p>ライセンス在庫不足通知：本文</p>`,
+    };
+  }
+
+  /**
+   * メールコンテンツを作成する(ライセンス不足)
+   * @param accountId 認証対象のユーザーが所属するアカウントのID
+   * @param userId 認証対象のユーザーのID
+   * @param email  認証対象のユーザーのメールアドレス
+   * @returns メールのサブジェクトとコンテンツ
+   */
+  async createMailContentOfLicenseExpiringSoon(): Promise<{
+    subject: string;
+    text: string;
+    html: string;
+  }> {
+    return {
+      subject: "ライセンス失効警告 ",
+      text: `ライセンス失効警告：本文`,
+      html: `<p>ライセンス失効警告：本文</p>`,
     };
   }
 
diff --git a/dictation_function/src/test/common/utility.ts b/dictation_function/src/test/common/utility.ts
new file mode 100644
index 0000000..cce735a
--- /dev/null
+++ b/dictation_function/src/test/common/utility.ts
@@ -0,0 +1,198 @@
+import { v4 as uuidv4 } from "uuid";
+import { DataSource } from "typeorm";
+import { User } from "../../entity/user.entity";
+import { Account } from "../../entity/account.entity";
+import { ADMIN_ROLES, USER_ROLES } from "../../constants";
+import { License } from "../../entity/license.entity";
+
+type InitialTestDBState = {
+  tier1Accounts: { account: Account; users: User[] }[];
+  tier2Accounts: { account: Account; users: User[] }[];
+  tier3Accounts: { account: Account; users: User[] }[];
+  tier4Accounts: { account: Account; users: User[] }[];
+  tier5Accounts: { account: Account; users: User[] }[];
+};
+
+// 上書きされたら困る項目を除外したAccount型
+type OverrideAccount = Omit<
+  Account,
+  "id" | "primary_admin_user_id" | "secondary_admin_user_id" | "user"
+>;
+
+// 上書きされたら困る項目を除外したUser型
+type OverrideUser = Omit<
+  User,
+  "id" | "account" | "license" | "userGroupMembers"
+>;
+
+type AccountDefault = { [K in keyof OverrideAccount]?: OverrideAccount[K] };
+type UserDefault = { [K in keyof OverrideUser]?: OverrideUser[K] };
+
+/**
+ * テスト ユーティリティ: 指定したプロパティを上書きしたユーザーを作成する
+ * @param dataSource データソース
+ * @param defaultUserValue User型と同等かつoptionalなプロパティを持つ上書き箇所指定用オブジェクト
+ * @returns 作成したユーザー
+ */
+export const makeTestUser = async (
+  datasource: DataSource,
+  defaultUserValue?: UserDefault
+): Promise<User> => {
+  const d = defaultUserValue;
+  const { identifiers } = await datasource.getRepository(User).insert({
+    account_id: d?.account_id ?? -1,
+    external_id: d?.external_id ?? uuidv4(),
+    role: d?.role ?? `${ADMIN_ROLES.STANDARD} ${USER_ROLES.NONE}`,
+    author_id: d?.author_id,
+    accepted_eula_version: d?.accepted_eula_version ?? "1.0",
+    accepted_dpa_version: d?.accepted_dpa_version ?? "1.0",
+    email_verified: d?.email_verified ?? true,
+    auto_renew: d?.auto_renew ?? true,
+    license_alert: d?.license_alert ?? true,
+    notification: d?.notification ?? true,
+    encryption: d?.encryption ?? true,
+    encryption_password: d?.encryption_password,
+    prompt: d?.prompt ?? true,
+    created_by: d?.created_by ?? "test_runner",
+    created_at: d?.created_at ?? new Date(),
+    updated_by: d?.updated_by ?? "updater",
+    updated_at: d?.updated_at ?? new Date(),
+  });
+  const result = identifiers.pop() as User;
+
+  const user = await datasource.getRepository(User).findOne({
+    where: {
+      id: result.id,
+    },
+  });
+  if (!user) {
+    throw new Error("Unexpected null");
+  }
+  return user;
+};
+
+/**
+ * テスト ユーティリティ: 指定したプロパティを上書きしたアカウントとその管理者ユーザーを作成する
+ * @param dataSource データソース
+ * @param defaultUserValue Account型と同等かつoptionalなプロパティを持つ上書き箇所指定用オブジェクト
+ * @param defaultAdminUserValue User型と同等かつoptionalなプロパティを持つ上書き箇所指定用オブジェクト(account_id等の所属関係が破壊される上書きは無視する)
+ * @returns 作成したアカウント
+ */
+export const makeTestAccount = async (
+  datasource: DataSource,
+  defaultAccountValue?: AccountDefault,
+  defaultAdminUserValue?: UserDefault,
+  isPrimaryAdminNotExist?: boolean,
+  isSecondaryAdminNotExist?: boolean
+): Promise<{ account: Account; admin: User }> => {
+  let accountId: number;
+  let userId: number;
+  {
+    const d = defaultAccountValue;
+    const { identifiers } = await datasource.getRepository(Account).insert({
+      tier: d?.tier ?? 1,
+      parent_account_id: d?.parent_account_id ?? undefined,
+      country: d?.country ?? "US",
+      delegation_permission: d?.delegation_permission ?? false,
+      locked: d?.locked ?? false,
+      company_name: d?.company_name ?? "test inc.",
+      verified: d?.verified ?? true,
+      deleted_at: d?.deleted_at ?? "",
+      created_by: d?.created_by ?? "test_runner",
+      created_at: d?.created_at ?? new Date(),
+      updated_by: d?.updated_by ?? "updater",
+      updated_at: d?.updated_at ?? new Date(),
+    });
+    const result = identifiers.pop() as Account;
+    accountId = result.id;
+  }
+  {
+    const d = defaultAdminUserValue;
+    const { identifiers } = await datasource.getRepository(User).insert({
+      external_id: d?.external_id ?? uuidv4(),
+      account_id: accountId,
+      role: d?.role ?? "admin none",
+      author_id: d?.author_id ?? undefined,
+      accepted_eula_version: d?.accepted_eula_version ?? "1.0",
+      accepted_dpa_version: d?.accepted_dpa_version ?? "1.0",
+      email_verified: d?.email_verified ?? true,
+      auto_renew: d?.auto_renew ?? true,
+      license_alert: d?.license_alert ?? true,
+      notification: d?.notification ?? true,
+      encryption: d?.encryption ?? true,
+      encryption_password: d?.encryption_password ?? "password",
+      prompt: d?.prompt ?? true,
+      deleted_at: d?.deleted_at ?? "",
+      created_by: d?.created_by ?? "test_runner",
+      created_at: d?.created_at ?? new Date(),
+      updated_by: d?.updated_by ?? "updater",
+      updated_at: d?.updated_at ?? new Date(),
+    });
+
+    const result = identifiers.pop() as User;
+    userId = result.id;
+  }
+
+  // Accountの管理者を設定する
+  let secondaryAdminUserId: number | null = null;
+  if (isPrimaryAdminNotExist && !isSecondaryAdminNotExist) {
+    secondaryAdminUserId = userId;
+  }
+  await datasource.getRepository(Account).update(
+    { id: accountId },
+    {
+      primary_admin_user_id: isPrimaryAdminNotExist ? null : userId,
+      secondary_admin_user_id: secondaryAdminUserId,
+    }
+  );
+
+  const account = await datasource.getRepository(Account).findOne({
+    where: {
+      id: accountId,
+    },
+  });
+
+  const admin = await datasource.getRepository(User).findOne({
+    where: {
+      id: userId,
+    },
+  });
+  if (!account || !admin) {
+    throw new Error("Unexpected null");
+  }
+
+  return {
+    account: account,
+    admin: admin,
+  };
+};
+
+export const createLicense = async (
+  datasource: DataSource,
+  licenseId: number,
+  expiry_date: Date | null,
+  accountId: number,
+  type: string,
+  status: string,
+  allocated_user_id: number | null,
+  order_id: number | null,
+  deleted_at: Date | null,
+  delete_order_id: number | null
+): Promise<void> => {
+  const { identifiers } = await datasource.getRepository(License).insert({
+    id: licenseId,
+    expiry_date: expiry_date,
+    account_id: accountId,
+    type: type,
+    status: status,
+    allocated_user_id: allocated_user_id,
+    order_id: order_id,
+    deleted_at: deleted_at,
+    delete_order_id: delete_order_id,
+    created_by: "test_runner",
+    created_at: new Date(),
+    updated_by: "updater",
+    updated_at: new Date(),
+  });
+  identifiers.pop() as License;
+};
diff --git a/dictation_function/src/test/licenseAlert.spec.ts b/dictation_function/src/test/licenseAlert.spec.ts
new file mode 100644
index 0000000..c94ec14
--- /dev/null
+++ b/dictation_function/src/test/licenseAlert.spec.ts
@@ -0,0 +1,339 @@
+import { DataSource } from "typeorm";
+import { licenseAlertProcessing } from "../functions/licenseAlert";
+import { makeTestAccount, createLicense } from "./common/utility";
+import * as dotenv from "dotenv";
+import {
+  DateWithDayEndTime,
+  DateWithZeroTime,
+  ExpirationThresholdDate,
+  NewTrialLicenseExpirationDate,
+} from "../common/types/types";
+import { AdB2cUser } from "../adb2c/types/types";
+import { ADB2C_SIGN_IN_TYPE } from "../constants";
+import { SendGridService } from "../sendgrid/sendgrid.service";
+import { AdB2cService } from "../adb2c/adb2c.service";
+import { InvocationContext } from "@azure/functions";
+
+describe("licenseAlert", () => {
+  dotenv.config({ path: ".env" });
+  dotenv.config({ path: ".env.local", override: true });
+  let source: DataSource | null = null;
+  beforeEach(async () => {
+    source = new DataSource({
+      type: "sqlite",
+      database: ":memory:",
+      logging: false,
+      entities: [__dirname + "/../../**/*.entity{.ts,.js}"],
+      synchronize: true, // trueにすると自動的にmigrationが行われるため注意
+    });
+    return source.initialize();
+  });
+
+  afterEach(async () => {
+    if (!source) return;
+    await source.destroy();
+    source = null;
+  });
+
+  it("ライセンス在庫不足メールが送信され、ライセンス失効警告メールが送信されないこと", async () => {
+    if (!source) fail();
+    const context = new InvocationContext();
+    const sendgridMock = new SendGridServiceMock() as SendGridService;
+    const adb2cMock = new AdB2cServiceMock() as AdB2cService;
+    // 呼び出し回数でテスト成否を判定
+    const spyShortage = jest.spyOn(
+      sendgridMock,
+      "createMailContentOfLicenseShortage"
+    );
+    const spyExpirySoon = jest.spyOn(
+      sendgridMock,
+      "createMailContentOfLicenseExpiringSoon"
+    );
+    const spySend = jest.spyOn(sendgridMock, "sendMail");
+
+    const currentDate = new DateWithZeroTime();
+    const expiringSoonDate = new ExpirationThresholdDate(currentDate.getTime());
+    const { account, admin } = await makeTestAccount(
+      source,
+      { tier: 5 },
+      { external_id: "external_id1" }
+    );
+    await createLicense(
+      source,
+      1,
+      expiringSoonDate,
+      account.id,
+      "STANDARD",
+      "Allocated",
+      admin.id,
+      null,
+      null,
+      null
+    );
+
+    await licenseAlertProcessing(context, source, sendgridMock, adb2cMock);
+    expect(spyShortage.mock.calls).toHaveLength(1);
+    expect(spyExpirySoon.mock.calls).toHaveLength(0);
+    expect(spySend.mock.calls).toHaveLength(1);
+  });
+
+  it("ライセンス在庫不足メール、ライセンス失効警告メールが送信されること", async () => {
+    if (!source) fail();
+    const context = new InvocationContext();
+    const sendgridMock = new SendGridServiceMock() as SendGridService;
+    const adb2cMock = new AdB2cServiceMock() as AdB2cService;
+
+    // 呼び出し回数でテスト成否を判定
+    const spyShortage = jest.spyOn(
+      sendgridMock,
+      "createMailContentOfLicenseShortage"
+    );
+    const spyExpirySoon = jest.spyOn(
+      sendgridMock,
+      "createMailContentOfLicenseExpiringSoon"
+    );
+    const spySend = jest.spyOn(sendgridMock, "sendMail");
+
+    const currentDate = new DateWithZeroTime();
+    const expiringSoonDate = new DateWithDayEndTime(currentDate.getTime());
+    const { account, admin } = await makeTestAccount(
+      source,
+      { tier: 5 },
+      { external_id: "external_id2", auto_renew: false }
+    );
+    await createLicense(
+      source,
+      1,
+      expiringSoonDate,
+      account.id,
+      "STANDARD",
+      "Allocated",
+      admin.id,
+      null,
+      null,
+      null
+    );
+
+    await licenseAlertProcessing(context, source, sendgridMock, adb2cMock);
+    expect(spyShortage.mock.calls).toHaveLength(1);
+    expect(spyExpirySoon.mock.calls).toHaveLength(1);
+    expect(spySend.mock.calls).toHaveLength(2);
+  });
+
+  it("在庫があるため、ライセンス在庫不足メールが送信されないこと", async () => {
+    if (!source) fail();
+    const context = new InvocationContext();
+    const sendgridMock = new SendGridServiceMock() as SendGridService;
+    const adb2cMock = new AdB2cServiceMock() as AdB2cService;
+
+    // 呼び出し回数でテスト成否を判定
+    const spyShortage = jest.spyOn(
+      sendgridMock,
+      "createMailContentOfLicenseShortage"
+    );
+    const spyExpirySoon = jest.spyOn(
+      sendgridMock,
+      "createMailContentOfLicenseExpiringSoon"
+    );
+    const spySend = jest.spyOn(sendgridMock, "sendMail");
+
+    const currentDate = new DateWithZeroTime();
+    const expiringSoonDate = new ExpirationThresholdDate(currentDate.getTime());
+    const expiryDate = new NewTrialLicenseExpirationDate(currentDate.getTime());
+    const { account, admin } = await makeTestAccount(
+      source,
+      { tier: 5 },
+      { external_id: "external_id3" }
+    );
+    await createLicense(
+      source,
+      1,
+      expiringSoonDate,
+      account.id,
+      "STANDARD",
+      "Allocated",
+      admin.id,
+      null,
+      null,
+      null
+    );
+    await createLicense(
+      source,
+      2,
+      expiryDate,
+      account.id,
+      "STANDARD",
+      "Unallocated",
+      null,
+      null,
+      null,
+      null
+    );
+
+    await licenseAlertProcessing(context, source, sendgridMock, adb2cMock);
+    expect(spyShortage.mock.calls).toHaveLength(0);
+    expect(spyExpirySoon.mock.calls).toHaveLength(0);
+    expect(spySend.mock.calls).toHaveLength(0);
+  });
+
+  it("AutoRenewがtureのため、ライセンス失効警告メールが送信されないこと", async () => {
+    if (!source) fail();
+    const context = new InvocationContext();
+    const sendgridMock = new SendGridServiceMock() as SendGridService;
+    const adb2cMock = new AdB2cServiceMock() as AdB2cService;
+
+    // 呼び出し回数でテスト成否を判定
+    const spyShortage = jest.spyOn(
+      sendgridMock,
+      "createMailContentOfLicenseShortage"
+    );
+    const spyExpirySoon = jest.spyOn(
+      sendgridMock,
+      "createMailContentOfLicenseExpiringSoon"
+    );
+    const spySend = jest.spyOn(sendgridMock, "sendMail");
+
+    const currentDate = new DateWithZeroTime();
+    const expiringSoonDate = new DateWithDayEndTime(currentDate.getTime());
+    const { account, admin } = await makeTestAccount(
+      source,
+      { tier: 5 },
+      { external_id: "external_id4", auto_renew: true }
+    );
+    await createLicense(
+      source,
+      1,
+      expiringSoonDate,
+      account.id,
+      "STANDARD",
+      "Allocated",
+      admin.id,
+      null,
+      null,
+      null
+    );
+
+    await licenseAlertProcessing(context, source, sendgridMock, adb2cMock);
+    expect(spyShortage.mock.calls).toHaveLength(1);
+    expect(spyExpirySoon.mock.calls).toHaveLength(0);
+    expect(spySend.mock.calls).toHaveLength(1);
+  });
+});
+
+// テスト用sendgrid
+export class SendGridServiceMock {
+  /**
+   * メールコンテンツを作成する(ライセンス不足)
+   * @param accountId 認証対象のユーザーが所属するアカウントのID
+   * @param userId 認証対象のユーザーのID
+   * @param email  認証対象のユーザーのメールアドレス
+   * @returns メールのサブジェクトとコンテンツ
+   */
+  async createMailContentOfLicenseShortage(): Promise<{
+    subject: string;
+    text: string;
+    html: string;
+  }> {
+    return {
+      subject: "ライセンス在庫不足通知",
+      text: `ライセンス在庫不足通知：本文`,
+      html: `<p>ライセンス在庫不足通知：本文</p>`,
+    };
+  }
+
+  /**
+   * メールコンテンツを作成する(ライセンス不足)
+   * @param accountId 認証対象のユーザーが所属するアカウントのID
+   * @param userId 認証対象のユーザーのID
+   * @param email  認証対象のユーザーのメールアドレス
+   * @returns メールのサブジェクトとコンテンツ
+   */
+  async createMailContentOfLicenseExpiringSoon(): Promise<{
+    subject: string;
+    text: string;
+    html: string;
+  }> {
+    return {
+      subject: "ライセンス失効警告",
+      text: `ライセンス失効警告：本文`,
+      html: `<p>ライセンス失効警告：本文</p>`,
+    };
+  }
+
+  /**
+   * メールを送信する
+   * @param to
+   * @param from
+   * @param subject
+   * @param text
+   * @param html
+   * @returns mail
+   */
+  async sendMail(
+    to: string,
+    from: string,
+    subject: string,
+    text: string,
+    html: string
+  ): Promise<void> {
+    return;
+  }
+}
+
+// テスト用adb2c
+export class AdB2cServiceMock {
+  /**
+   * Azure AD B2Cからユーザ情報を取得する
+   * @param externalIds 外部ユーザーID
+   * @returns ユーザ情報
+   */
+  async getUsers(externalIds: string[]): Promise<AdB2cUser[]> {
+    const AdB2cMockUsers: AdB2cUser[] = [
+      {
+        id: "external_id1",
+        displayName: "test1",
+        identities: [
+          {
+            signInType: ADB2C_SIGN_IN_TYPE.EMAILADDRESS,
+            issuer: "issuer",
+            issuerAssignedId: "test1@mail.com",
+          },
+        ],
+      },
+      {
+        id: "external_id2",
+        displayName: "test2",
+        identities: [
+          {
+            signInType: ADB2C_SIGN_IN_TYPE.EMAILADDRESS,
+            issuer: "issuer",
+            issuerAssignedId: "test2@mail.com",
+          },
+        ],
+      },
+      {
+        id: "external_id3",
+        displayName: "test3",
+        identities: [
+          {
+            signInType: ADB2C_SIGN_IN_TYPE.EMAILADDRESS,
+            issuer: "issuer",
+            issuerAssignedId: "test3@mail.com",
+          },
+        ],
+      },
+      {
+        id: "external_id4",
+        displayName: "test4",
+        identities: [
+          {
+            signInType: ADB2C_SIGN_IN_TYPE.EMAILADDRESS,
+            issuer: "issuer",
+            issuerAssignedId: "test4@mail.com",
+          },
+        ],
+      },
+    ];
+    return AdB2cMockUsers;
+  }
+}
diff --git a/dictation_function/src/test/timerTriggerExample.spec.ts b/dictation_function/src/test/timerTriggerExample.spec.ts
deleted file mode 100644
index 5d30ff9..0000000
--- a/dictation_function/src/test/timerTriggerExample.spec.ts
+++ /dev/null
@@ -1,42 +0,0 @@
-import { DataSource } from "typeorm";
-import {
-  testExample,
-  testSendgridExample,
-} from "../functions/timerTriggerExample";
-import { makeTestUser } from "../common/test/utility";
-import * as dotenv from "dotenv";
-
-describe("timerTriggerExample", () => {
-  dotenv.config({ path: ".env.local", override: true });
-  let source: DataSource | null = null;
-  beforeEach(async () => {
-    source = new DataSource({
-      type: "sqlite",
-      database: ":memory:",
-      logging: false,
-      entities: [__dirname + "/../../**/*.entity{.ts,.js}"],
-      synchronize: true, // trueにすると自動的にmigrationが行われるため注意
-    });
-    return source.initialize();
-  });
-
-  afterEach(async () => {
-    if (!source) return;
-    await source.destroy();
-    source = null;
-  });
-
-  it("sample test(DB)", async () => {
-    const count = 5;
-    for (let i = 0; i < count; i++) {
-      await makeTestUser(source);
-    }
-
-    const result = await testExample(source);
-    expect(result.length).toEqual(count);
-  });
-
-  it("sample test(sendgrid)", async () => {
-    await testSendgridExample();
-  });
-});
diff --git a/dictation_function/tsconfig.json b/dictation_function/tsconfig.json
index 4e3609a..dd9c7a4 100644
--- a/dictation_function/tsconfig.json
+++ b/dictation_function/tsconfig.json
@@ -8,6 +8,7 @@
     "strict": false,
     "emitDecoratorMetadata": true,
     "experimentalDecorators": true,
-    "esModuleInterop": true
+    "esModuleInterop": true,
+    "strictNullChecks": true,
   }
 }
\ No newline at end of file
diff --git a/dictation_server/src/common/cache/constants.ts b/dictation_server/src/common/cache/constants.ts
index b79dd78..9f588f6 100644
--- a/dictation_server/src/common/cache/constants.ts
+++ b/dictation_server/src/common/cache/constants.ts
@@ -1 +1,3 @@
 export const ADB2C_PREFIX = 'adb2c-external-id:';
+
+export const IDTOKEN_PREFIX = 'id-token:';
diff --git a/dictation_server/src/common/cache/index.ts b/dictation_server/src/common/cache/index.ts
index 3355a54..4985492 100644
--- a/dictation_server/src/common/cache/index.ts
+++ b/dictation_server/src/common/cache/index.ts
@@ -1,4 +1,4 @@
-import { ADB2C_PREFIX } from './constants';
+import { ADB2C_PREFIX, IDTOKEN_PREFIX } from './constants';
 
 /**
  * ADB2Cのユーザー格納用のキーを生成する
@@ -17,3 +17,12 @@ export const makeADB2CKey = (externalId: string): string => {
 export const restoreAdB2cID = (key: string): string => {
   return key.replace(ADB2C_PREFIX, '');
 };
+
+/**
+ * ADB2CのIDトークン格納用のキーを生成する
+ * @param idToken IDトークン
+ * @returns キャッシュのキー
+ */
+export const makeIDTokenKey = (idToken: string): string => {
+  return `${IDTOKEN_PREFIX}${idToken}`;
+};
diff --git a/dictation_server/src/common/test/modules.ts b/dictation_server/src/common/test/modules.ts
index 9c3d578..61c0396 100644
--- a/dictation_server/src/common/test/modules.ts
+++ b/dictation_server/src/common/test/modules.ts
@@ -38,6 +38,8 @@ import { TermsService } from '../../features/terms/terms.service';
 import { TermsRepositoryModule } from '../../repositories/terms/terms.repository.module';
 import { TermsModule } from '../../features/terms/terms.module';
 import { CacheModule } from '@nestjs/common';
+import { RedisModule } from '../../gateways/redis/redis.module';
+import { RedisService } from '../../gateways/redis/redis.service';
 
 export const makeTestingModule = async (
   datasource: DataSource,
@@ -77,6 +79,7 @@ export const makeTestingModule = async (
         SortCriteriaRepositoryModule,
         WorktypesRepositoryModule,
         TermsRepositoryModule,
+        RedisModule,
         CacheModule.register({ isGlobal: true }),
       ],
       providers: [
@@ -90,6 +93,7 @@ export const makeTestingModule = async (
         TemplatesService,
         WorkflowsService,
         TermsService,
+        RedisService,
       ],
     })
       .useMocker(async (token) => {
diff --git a/dictation_server/src/features/auth/auth.controller.ts b/dictation_server/src/features/auth/auth.controller.ts
index a07b666..32d7697 100644
--- a/dictation_server/src/features/auth/auth.controller.ts
+++ b/dictation_server/src/features/auth/auth.controller.ts
@@ -33,6 +33,8 @@ import { RoleGuard } from '../../common/guards/role/roleguards';
 import { ADMIN_ROLES, TIERS } from '../../constants';
 import jwt from 'jsonwebtoken';
 import { AccessToken, RefreshToken } from '../../common/token';
+import { makeIDTokenKey } from '../../common/cache';
+import { RedisService } from '../../gateways/redis/redis.service';
 
 @ApiTags('auth')
 @Controller('auth')
@@ -41,6 +43,7 @@ export class AuthController {
     // TODO「タスク 1828: IDトークンを一度しか使えないようにする」で使用する予定
     // private readonly redisService: RedisService,
     private readonly authService: AuthService,
+    private readonly redisService: RedisService,
   ) {}
 
   @Post('token')
@@ -77,6 +80,18 @@ export class AuthController {
 
     const context = makeContext(uuidv4());
 
+    const key = makeIDTokenKey(body.idToken);
+    const isTokenExists = await this.redisService.get<boolean>(key);
+    if (!isTokenExists) {
+      // IDトークンがキャッシュに存在しない場合(idTokenの有効期限をADB2Cの有効期限と合わせる(300秒))
+      await this.redisService.set(key, true, 300);
+    } else {
+      // IDトークンがキャッシュに存在する場合エラー
+      throw new HttpException(
+        makeErrorResponse('E000106'),
+        HttpStatus.UNAUTHORIZED,
+      );
+    }
     // 同意済み利用規約バージョンが最新かチェック
     const isAcceptedLatestVersion =
       await this.authService.isAcceptedLatestVersion(context, idToken);
diff --git a/dictation_server/src/features/auth/auth.module.ts b/dictation_server/src/features/auth/auth.module.ts
index 2e3dc4c..d86bf30 100644
--- a/dictation_server/src/features/auth/auth.module.ts
+++ b/dictation_server/src/features/auth/auth.module.ts
@@ -4,15 +4,10 @@ import { AdB2cModule } from '../../gateways/adb2c/adb2c.module';
 import { UsersRepositoryModule } from '../../repositories/users/users.repository.module';
 import { AuthController } from './auth.controller';
 import { AuthService } from './auth.service';
-import { TermsRepositoryModule } from '../../repositories/terms/terms.repository.module';
+import { RedisService } from '../../gateways/redis/redis.service';
 @Module({
-  imports: [
-    ConfigModule,
-    AdB2cModule,
-    UsersRepositoryModule,
-    TermsRepositoryModule,
-  ],
+  imports: [ConfigModule, AdB2cModule, UsersRepositoryModule],
   controllers: [AuthController],
-  providers: [AuthService],
+  providers: [AuthService, RedisService],
 })
 export class AuthModule {}
diff --git a/dictation_server/src/repositories/accounts/accounts.repository.service.ts b/dictation_server/src/repositories/accounts/accounts.repository.service.ts
index 65fe99d..8380461 100644
--- a/dictation_server/src/repositories/accounts/accounts.repository.service.ts
+++ b/dictation_server/src/repositories/accounts/accounts.repository.service.ts
@@ -886,11 +886,12 @@ export class AccountsRepositoryService {
           where: {
             id: primaryAdminUserId,
             account_id: myAccountId,
+            email_verified: true,
           },
         });
         if (!primaryAdminUser) {
           throw new AdminUserNotFoundError(
-            `Primary admin user is not found. id: ${primaryAdminUserId}, account_id: ${myAccountId}`,
+            `Primary admin user is not found or email not verified. id: ${primaryAdminUserId}, account_id: ${myAccountId}`,
           );
         }
       }
@@ -901,11 +902,12 @@ export class AccountsRepositoryService {
           where: {
             id: secondryAdminUserId,
             account_id: myAccountId,
+            email_verified: true,
           },
         });
         if (!secondryAdminUser) {
           throw new AdminUserNotFoundError(
-            `Secondry admin user is not found. id: ${secondryAdminUserId}, account_id: ${myAccountId}`,
+            `Secondary admin user is not found or email not verified. id: ${secondryAdminUserId}, account_id: ${myAccountId}`,
           );
         }
       }