diff --git a/apps/browser/src/autofill/background/overlay.background.spec.ts b/apps/browser/src/autofill/background/overlay.background.spec.ts
index fc53ca4f296..72b17a14d30 100644
--- a/apps/browser/src/autofill/background/overlay.background.spec.ts
+++ b/apps/browser/src/autofill/background/overlay.background.spec.ts
@@ -3604,9 +3604,10 @@ describe("OverlayBackground", () => {
       });
 
       it("sends a message to the list port indicating that the generated password should be updated", async () => {
-        sendPortMessage(listMessageConnectorSpy, { command: "refreshGeneratedPassword", portKey });
         overlayBackground["credential$"].next("refresh");
 
+        sendPortMessage(listMessageConnectorSpy, { command: "refreshGeneratedPassword", portKey });
+
         await flushPromises();
 
         expect(listPortSpy.postMessage).toHaveBeenCalledWith({
diff --git a/apps/browser/src/autofill/background/overlay.background.ts b/apps/browser/src/autofill/background/overlay.background.ts
index 6870c0b096c..61612ce0486 100644
--- a/apps/browser/src/autofill/background/overlay.background.ts
+++ b/apps/browser/src/autofill/background/overlay.background.ts
@@ -1822,8 +1822,8 @@ export class OverlayBackground implements OverlayBackgroundInterface {
   /**
    * Generates a password based on the user defined password generation options.
    */
-  private requestGeneratedPassword(source: GenerateRequest["source"]) {
-    this.requestGeneratedPassword$.next({ source, type: Type.password });
+  private requestGeneratedPassword(request: GenerateRequest) {
+    this.requestGeneratedPassword$.next(request);
   }
 
   /**
@@ -1840,7 +1840,7 @@ export class OverlayBackground implements OverlayBackgroundInterface {
    */
   private async updateGeneratedPassword(refreshPassword: boolean = false) {
     if (!this.credential$.value || refreshPassword) {
-      this.requestGeneratedPassword("inline-menu");
+      this.requestGeneratedPassword({ source: "inline-menu", type: Type.password });
     }
 
     this.postMessageToPort(this.inlineMenuListPort, {
@@ -3105,7 +3105,7 @@ export class OverlayBackground implements OverlayBackgroundInterface {
     }
 
     if (!this.credential$.value) {
-      this.requestGeneratedPassword("inline-menu.init");
+      this.requestGeneratedPassword({ source: "inline-menu.init", type: Type.password });
     }
 
     return true;
diff --git a/apps/browser/src/background/commands.background.ts b/apps/browser/src/background/commands.background.ts
index 696fd5c4f05..f115be56992 100644
--- a/apps/browser/src/background/commands.background.ts
+++ b/apps/browser/src/background/commands.background.ts
@@ -1,6 +1,6 @@
 // FIXME: Update this file to be type safe and remove this and next line
 // @ts-strict-ignore
-import { firstValueFrom } from "rxjs";
+import { firstValueFrom, Observable } from "rxjs";
 
 import { LockService } from "@bitwarden/auth/common";
 import { AccountService } from "@bitwarden/common/auth/abstractions/account.service";
@@ -26,7 +26,7 @@ export default class CommandsBackground {
     private main: MainBackground,
     private platformUtilsService: PlatformUtilsService,
     private authService: AuthService,
-    private generatePasswordToClipboard: () => Promise<void>,
+    private generatePasswordToClipboard: () => Observable<string>,
     private accountService: AccountService,
     private lockService: LockService,
   ) {
@@ -53,8 +53,8 @@ export default class CommandsBackground {
 
   private async processCommand(command: string, sender?: chrome.runtime.MessageSender) {
     switch (command) {
-      case "generate_password":
-        await this.generatePasswordToClipboard();
+      case ExtensionCommand.GeneratePassword:
+        this.generatePasswordToClipboard();
         break;
       case ExtensionCommand.AutofillLogin:
         await this.triggerAutofillCommand(
@@ -74,10 +74,10 @@ export default class CommandsBackground {
           ExtensionCommand.AutofillIdentity,
         );
         break;
-      case "open_popup":
+      case ExtensionCommand.OpenPopup:
         await this.openPopup();
         break;
-      case "lock_vault": {
+      case ExtensionCommand.LockVault: {
         const activeUserId = await firstValueFrom(getUserId(this.accountService.activeAccount$));
         await this.lockService.lock(activeUserId);
         break;
diff --git a/apps/browser/src/background/main.background.ts b/apps/browser/src/background/main.background.ts
index ff10bfb826c..4e485e6aeb2 100644
--- a/apps/browser/src/background/main.background.ts
+++ b/apps/browser/src/background/main.background.ts
@@ -2060,12 +2060,15 @@ export default class MainBackground {
     );
   };
 
-  generatePasswordToClipboard = async () => {
-    const { credential: password } = await firstValueFrom(
-      this.yieldGeneratedPassword(of({ source: "clipboard", type: Type.password })),
+  generatePasswordToClipboard = () => {
+    return this.yieldGeneratedPassword(of({ source: "clipboard", type: Type.password })).pipe(
+      concatMap(async (generated) => {
+        this.platformUtilsService.copyToClipboard(generated.credential);
+        await this.addPasswordToHistory(generated.credential);
+
+        return generated.credential;
+      }),
     );
-    this.platformUtilsService.copyToClipboard(password);
-    await this.addPasswordToHistory(password);
   };
 
   addPasswordToHistory = async (password: string) => {