diff --git a/apps/browser/src/autofill/browser/cipher-context-menu-handler.spec.ts b/apps/browser/src/autofill/browser/cipher-context-menu-handler.spec.ts
index 53d3d10076..9db6574aad 100644
--- a/apps/browser/src/autofill/browser/cipher-context-menu-handler.spec.ts
+++ b/apps/browser/src/autofill/browser/cipher-context-menu-handler.spec.ts
@@ -96,7 +96,7 @@ describe("CipherContextMenuHandler", () => {
 
       expect(cipherService.getAllDecryptedForUrl).toHaveBeenCalledWith("https://test.com");
 
-      expect(mainContextMenuHandler.loadOptions).toHaveBeenCalledTimes(1);
+      expect(mainContextMenuHandler.loadOptions).toHaveBeenCalledTimes(2);
 
       expect(mainContextMenuHandler.loadOptions).toHaveBeenCalledWith(
         "Test Cipher (Test Username)",
diff --git a/apps/browser/src/autofill/browser/cipher-context-menu-handler.ts b/apps/browser/src/autofill/browser/cipher-context-menu-handler.ts
index d4f72e5663..fe6479aae5 100644
--- a/apps/browser/src/autofill/browser/cipher-context-menu-handler.ts
+++ b/apps/browser/src/autofill/browser/cipher-context-menu-handler.ts
@@ -4,7 +4,6 @@ import { StateFactory } from "@bitwarden/common/platform/factories/state-factory
 import { Utils } from "@bitwarden/common/platform/misc/utils";
 import { GlobalState } from "@bitwarden/common/platform/models/domain/global-state";
 import { CipherService } from "@bitwarden/common/vault/abstractions/cipher.service";
-import { CipherRepromptType } from "@bitwarden/common/vault/enums/cipher-reprompt-type";
 import { CipherType } from "@bitwarden/common/vault/enums/cipher-type";
 import { CipherView } from "@bitwarden/common/vault/models/view/cipher.view";
 
@@ -177,11 +176,7 @@ export class CipherContextMenuHandler {
   }
 
   private async updateForCipher(url: string, cipher: CipherView) {
-    if (
-      cipher == null ||
-      cipher.type !== CipherType.Login ||
-      cipher.reprompt !== CipherRepromptType.None
-    ) {
+    if (cipher == null || cipher.type !== CipherType.Login) {
       return;
     }
 
diff --git a/apps/browser/src/autofill/browser/context-menu-clicked-handler.ts b/apps/browser/src/autofill/browser/context-menu-clicked-handler.ts
index a5cf1c7065..38e605abe7 100644
--- a/apps/browser/src/autofill/browser/context-menu-clicked-handler.ts
+++ b/apps/browser/src/autofill/browser/context-menu-clicked-handler.ts
@@ -203,17 +203,45 @@ export class ContextMenuClickedHandler {
         if (tab == null) {
           return;
         }
-        await this.autofillAction(tab, cipher);
+
+        if (cipher.reprompt !== CipherRepromptType.None) {
+          await BrowserApi.tabSendMessageData(tab, "passwordReprompt", {
+            cipherId: cipher.id,
+            action: AUTOFILL_ID,
+          });
+        } else {
+          await this.autofillAction(tab, cipher);
+        }
+
         break;
       case COPY_USERNAME_ID:
         this.copyToClipboard({ text: cipher.login.username, tab: tab });
         break;
       case COPY_PASSWORD_ID:
-        this.copyToClipboard({ text: cipher.login.password, tab: tab });
-        this.eventCollectionService.collect(EventType.Cipher_ClientCopiedPassword, cipher.id);
+        if (cipher.reprompt !== CipherRepromptType.None) {
+          await BrowserApi.tabSendMessageData(tab, "passwordReprompt", {
+            cipherId: cipher.id,
+            action: COPY_PASSWORD_ID,
+          });
+        } else {
+          this.copyToClipboard({ text: cipher.login.password, tab: tab });
+          this.eventCollectionService.collect(EventType.Cipher_ClientCopiedPassword, cipher.id);
+        }
+
         break;
       case COPY_VERIFICATIONCODE_ID:
-        this.copyToClipboard({ text: await this.totpService.getCode(cipher.login.totp), tab: tab });
+        if (cipher.reprompt !== CipherRepromptType.None) {
+          await BrowserApi.tabSendMessageData(tab, "passwordReprompt", {
+            cipherId: cipher.id,
+            action: COPY_VERIFICATIONCODE_ID,
+          });
+        } else {
+          this.copyToClipboard({
+            text: await this.totpService.getCode(cipher.login.totp),
+            tab: tab,
+          });
+        }
+
         break;
     }
   }
diff --git a/apps/browser/src/autofill/content/message_handler.ts b/apps/browser/src/autofill/content/message_handler.ts
index 5302a5042b..5ef0abdb7c 100644
--- a/apps/browser/src/autofill/content/message_handler.ts
+++ b/apps/browser/src/autofill/content/message_handler.ts
@@ -28,6 +28,7 @@ window.addEventListener(
 
 const forwardCommands = [
   "promptForLogin",
+  "passwordReprompt",
   "addToLockedVaultPendingNotifications",
   "unlockCompleted",
   "addedCipher",
diff --git a/apps/browser/src/autofill/services/autofill.service.ts b/apps/browser/src/autofill/services/autofill.service.ts
index 9ced0104b8..8b7ec91653 100644
--- a/apps/browser/src/autofill/services/autofill.service.ts
+++ b/apps/browser/src/autofill/services/autofill.service.ts
@@ -234,7 +234,16 @@ export default class AutofillService implements AutofillServiceInterface {
       }
     }
 
-    if (cipher == null || cipher.reprompt !== CipherRepromptType.None) {
+    if (cipher == null) {
+      return null;
+    }
+
+    if (cipher.reprompt !== CipherRepromptType.None) {
+      await BrowserApi.tabSendMessageData(tab, "passwordReprompt", {
+        cipherId: cipher.id,
+        action: "autofill",
+      });
+
       return null;
     }
 
diff --git a/apps/browser/src/background/runtime.background.ts b/apps/browser/src/background/runtime.background.ts
index 2e9fc93488..ee15c0a3b9 100644
--- a/apps/browser/src/background/runtime.background.ts
+++ b/apps/browser/src/background/runtime.background.ts
@@ -61,6 +61,8 @@ export default class RuntimeBackground {
   }
 
   async processMessage(msg: any, sender: chrome.runtime.MessageSender, sendResponse: any) {
+    const cipherId = msg.data?.cipherId;
+
     switch (msg.command) {
       case "loggedIn":
       case "unlocked": {
@@ -68,7 +70,7 @@ export default class RuntimeBackground {
 
         if (this.lockedVaultPendingNotifications?.length > 0) {
           item = this.lockedVaultPendingNotifications.pop();
-          await this.browserPopoutWindowService.closeLoginPrompt();
+          await this.browserPopoutWindowService.closeUnlockPrompt();
         }
 
         await this.main.refreshBadge();
@@ -108,13 +110,22 @@ export default class RuntimeBackground {
         break;
       case "promptForLogin":
       case "bgReopenPromptForLogin":
-        await this.browserPopoutWindowService.openLoginPrompt(sender.tab?.windowId);
+        await this.browserPopoutWindowService.openUnlockPrompt(sender.tab?.windowId);
+        break;
+      case "passwordReprompt":
+        if (cipherId) {
+          await this.browserPopoutWindowService.openPasswordRepromptPrompt(sender.tab?.windowId, {
+            cipherId: cipherId,
+            senderTabId: sender.tab.id,
+            action: msg.data?.action,
+          });
+        }
         break;
       case "openAddEditCipher": {
         const addEditCipherUrl =
-          msg.data?.cipherId == null
+          cipherId == null
             ? "popup/index.html#/edit-cipher"
-            : "popup/index.html#/edit-cipher?cipherId=" + msg.data.cipherId;
+            : "popup/index.html#/edit-cipher?cipherId=" + cipherId;
 
         BrowserApi.openBitwardenExtensionTab(addEditCipherUrl, true);
         break;
diff --git a/apps/browser/src/platform/browser/browser-api.ts b/apps/browser/src/platform/browser/browser-api.ts
index 243971dbfc..675fd0b119 100644
--- a/apps/browser/src/platform/browser/browser-api.ts
+++ b/apps/browser/src/platform/browser/browser-api.ts
@@ -42,11 +42,20 @@ export class BrowserApi {
     });
   }
 
-  static async getTab(tabId: number) {
-    if (tabId == null) {
+  static async getTab(tabId: number): Promise<chrome.tabs.Tab> | null {
+    if (!tabId) {
       return null;
     }
-    return await chrome.tabs.get(tabId);
+
+    if (BrowserApi.manifestVersion === 3) {
+      return await chrome.tabs.get(tabId);
+    }
+
+    return new Promise((resolve) =>
+      chrome.tabs.get(tabId, (tab) => {
+        resolve(tab);
+      })
+    );
   }
 
   static async getTabFromCurrentWindow(): Promise<chrome.tabs.Tab> | null {
diff --git a/apps/browser/src/platform/popup/abstractions/browser-popout-window.service.ts b/apps/browser/src/platform/popup/abstractions/browser-popout-window.service.ts
index ca22e369d8..0b3f55ee99 100644
--- a/apps/browser/src/platform/popup/abstractions/browser-popout-window.service.ts
+++ b/apps/browser/src/platform/popup/abstractions/browser-popout-window.service.ts
@@ -1,6 +1,15 @@
 interface BrowserPopoutWindowService {
-  openLoginPrompt(senderWindowId: number): Promise<void>;
-  closeLoginPrompt(): Promise<void>;
+  openUnlockPrompt(senderWindowId: number): Promise<void>;
+  closeUnlockPrompt(): Promise<void>;
+  openPasswordRepromptPrompt(
+    senderWindowId: number,
+    promptData: {
+      action: string;
+      cipherId: string;
+      senderTabId: number;
+    }
+  ): Promise<void>;
+  closePasswordRepromptPrompt(): Promise<void>;
 }
 
 export { BrowserPopoutWindowService };
diff --git a/apps/browser/src/platform/popup/browser-popout-window.service.ts b/apps/browser/src/platform/popup/browser-popout-window.service.ts
index bfec3e690b..95be15cc20 100644
--- a/apps/browser/src/platform/popup/browser-popout-window.service.ts
+++ b/apps/browser/src/platform/popup/browser-popout-window.service.ts
@@ -11,20 +11,48 @@ class BrowserPopoutWindowService implements BrowserPopupWindowServiceInterface {
     height: 800,
   };
 
-  async openLoginPrompt(senderWindowId: number) {
-    await this.closeLoginPrompt();
-    await this.openPopoutWindow(
+  async openUnlockPrompt(senderWindowId: number) {
+    await this.closeUnlockPrompt();
+    await this.openSingleActionPopout(
       senderWindowId,
       "popup/index.html?uilocation=popout",
-      "loginPrompt"
+      "unlockPrompt"
     );
   }
 
-  async closeLoginPrompt() {
-    await this.closeSingleActionPopout("loginPrompt");
+  async closeUnlockPrompt() {
+    await this.closeSingleActionPopout("unlockPrompt");
   }
 
-  private async openPopoutWindow(
+  async openPasswordRepromptPrompt(
+    senderWindowId: number,
+    {
+      cipherId,
+      senderTabId,
+      action,
+    }: {
+      cipherId: string;
+      senderTabId: number;
+      action: string;
+    }
+  ) {
+    await this.closePasswordRepromptPrompt();
+
+    const promptWindowPath =
+      "popup/index.html#/view-cipher" +
+      "?uilocation=popout" +
+      `&cipherId=${cipherId}` +
+      `&senderTabId=${senderTabId}` +
+      `&action=${action}`;
+
+    await this.openSingleActionPopout(senderWindowId, promptWindowPath, "passwordReprompt");
+  }
+
+  async closePasswordRepromptPrompt() {
+    await this.closeSingleActionPopout("passwordReprompt");
+  }
+
+  private async openSingleActionPopout(
     senderWindowId: number,
     popupWindowURL: string,
     singleActionPopoutKey: string
diff --git a/apps/browser/src/vault/popup/components/vault/view.component.html b/apps/browser/src/vault/popup/components/vault/view.component.html
index 7b313ab117..e8dceaff09 100644
--- a/apps/browser/src/vault/popup/components/vault/view.component.html
+++ b/apps/browser/src/vault/popup/components/vault/view.component.html
@@ -555,7 +555,11 @@
         class="box-content-row"
         appStopClick
         (click)="fillCipher()"
-        *ngIf="cipher.type !== cipherType.SecureNote && !cipher.isDeleted && !inPopout"
+        *ngIf="
+          cipher.type !== cipherType.SecureNote &&
+          !cipher.isDeleted &&
+          (!this.inPopout || this.loadAction)
+        "
       >
         <div class="row-main text-primary">
           <div class="icon text-primary" aria-hidden="true">
diff --git a/apps/browser/src/vault/popup/components/vault/view.component.ts b/apps/browser/src/vault/popup/components/vault/view.component.ts
index aa17c16f26..34f2cacde1 100644
--- a/apps/browser/src/vault/popup/components/vault/view.component.ts
+++ b/apps/browser/src/vault/popup/components/vault/view.component.ts
@@ -1,6 +1,7 @@
 import { Location } from "@angular/common";
 import { ChangeDetectorRef, Component, NgZone } from "@angular/core";
 import { ActivatedRoute, Router } from "@angular/router";
+import { Subject, takeUntil } from "rxjs";
 import { first } from "rxjs/operators";
 
 import { DialogServiceAbstraction } from "@bitwarden/angular/services/dialog";
@@ -31,6 +32,17 @@ import { PopupUtilsService } from "../../../../popup/services/popup-utils.servic
 
 const BroadcasterSubscriptionId = "ChildViewComponent";
 
+export const AUTOFILL_ID = "autofill";
+export const COPY_USERNAME_ID = "copy-username";
+export const COPY_PASSWORD_ID = "copy-password";
+export const COPY_VERIFICATIONCODE_ID = "copy-totp";
+
+type LoadAction =
+  | typeof AUTOFILL_ID
+  | typeof COPY_USERNAME_ID
+  | typeof COPY_PASSWORD_ID
+  | typeof COPY_VERIFICATIONCODE_ID;
+
 @Component({
   selector: "app-vault-view",
   templateUrl: "view.component.html",
@@ -39,10 +51,15 @@ export class ViewComponent extends BaseViewComponent {
   showAttachments = true;
   pageDetails: any[] = [];
   tab: any;
+  senderTabId?: number;
+  loadAction?: LoadAction;
+  uilocation?: "popout" | "popup" | "sidebar" | "tab";
   loadPageDetailsTimeout: number;
   inPopout = false;
   cipherType = CipherType;
 
+  private destroy$ = new Subject<void>();
+
   constructor(
     cipherService: CipherService,
     folderService: FolderService,
@@ -93,7 +110,14 @@ export class ViewComponent extends BaseViewComponent {
   }
 
   ngOnInit() {
-    this.inPopout = this.popupUtilsService.inPopout(window);
+    this.route.queryParams.pipe(takeUntil(this.destroy$)).subscribe((value) => {
+      this.loadAction = value?.action;
+      this.senderTabId = parseInt(value?.senderTabId, 10) || undefined;
+      this.uilocation = value?.uilocation;
+    });
+
+    this.inPopout = this.uilocation === "popout" || this.popupUtilsService.inPopout(window);
+
     // eslint-disable-next-line rxjs-angular/prefer-takeuntil, rxjs/no-async-subscribe
     this.route.queryParams.pipe(first()).subscribe(async (params) => {
       if (params.cipherId) {
@@ -134,6 +158,8 @@ export class ViewComponent extends BaseViewComponent {
   }
 
   ngOnDestroy() {
+    this.destroy$.next();
+    this.destroy$.complete();
     super.ngOnDestroy();
     this.broadcasterService.unsubscribe(BroadcasterSubscriptionId);
   }
@@ -141,6 +167,27 @@ export class ViewComponent extends BaseViewComponent {
   async load() {
     await super.load();
     await this.loadPageDetails();
+
+    switch (this.loadAction) {
+      case AUTOFILL_ID:
+        this.fillCipher();
+        return;
+      case COPY_USERNAME_ID:
+        await this.copy(this.cipher.login.username, "username", "Username");
+        break;
+      case COPY_PASSWORD_ID:
+        await this.copy(this.cipher.login.password, "password", "Password");
+        break;
+      case COPY_VERIFICATIONCODE_ID:
+        await this.copy(this.cipher.login.totp, "verificationCodeTotp", "TOTP");
+        break;
+      default:
+        break;
+    }
+
+    if (this.inPopout && this.loadAction) {
+      this.close();
+    }
   }
 
   async edit() {
@@ -191,6 +238,10 @@ export class ViewComponent extends BaseViewComponent {
     const didAutofill = await this.doAutofill();
     if (didAutofill) {
       this.platformUtilsService.showToast("success", null, this.i18nService.t("autoFillSuccess"));
+
+      if (this.inPopout) {
+        this.close();
+      }
     }
   }
 
@@ -255,15 +306,30 @@ export class ViewComponent extends BaseViewComponent {
   }
 
   close() {
+    if (this.senderTabId) {
+      BrowserApi.focusTab(this.senderTabId);
+    }
+
+    if (this.inPopout) {
+      window.close();
+      return;
+    }
+
     this.location.back();
   }
 
   private async loadPageDetails() {
     this.pageDetails = [];
     this.tab = await BrowserApi.getTabFromCurrentWindow();
-    if (this.tab == null) {
+
+    if (this.senderTabId) {
+      this.tab = await BrowserApi.getTab(this.senderTabId);
+    }
+
+    if (!this.tab) {
       return;
     }
+
     BrowserApi.tabSendMessage(this.tab, {
       command: "collectPageDetails",
       tab: this.tab,