diff --git a/apps/browser/src/_locales/en/messages.json b/apps/browser/src/_locales/en/messages.json
index 5cc7c30bfb4c..134029df1e48 100644
--- a/apps/browser/src/_locales/en/messages.json
+++ b/apps/browser/src/_locales/en/messages.json
@@ -5830,6 +5830,9 @@
   "settingDisabledByPolicy": {
     "message": "This setting is disabled by your organization's policy.",
     "description": "This hint text is displayed when a user setting is disabled due to an organization policy."
+  }, 
+  "importPopoutDialogDesc": {
+    "message": "To import from a file, you need to pop out the extension to a new window."
   },
   "zipPostalCodeLabel": {
     "message": "ZIP / Postal code"
diff --git a/apps/browser/src/popup/app-routing.module.ts b/apps/browser/src/popup/app-routing.module.ts
index a36396afa1ab..e3471e89fb22 100644
--- a/apps/browser/src/popup/app-routing.module.ts
+++ b/apps/browser/src/popup/app-routing.module.ts
@@ -324,7 +324,7 @@ const routes: Routes = [
     path: "add-send",
     component: SendAddEditV2Component,
     canActivate: [authGuard],
-    data: { elevation: 1 } satisfies RouteDataProperties,
+    data: { elevation: 1, doNotSaveUrl: true } satisfies RouteDataProperties,
   },
   {
     path: "edit-send",
diff --git a/apps/browser/src/tools/popup/send-v2/send-file-popout-dialog/send-file-popout-dialog-container.component.ts b/apps/browser/src/tools/popup/send-v2/send-file-popout-dialog/send-file-popout-dialog-container.component.ts
index 1f0d9f2a0c9c..c7ab6f925b08 100644
--- a/apps/browser/src/tools/popup/send-v2/send-file-popout-dialog/send-file-popout-dialog-container.component.ts
+++ b/apps/browser/src/tools/popup/send-v2/send-file-popout-dialog/send-file-popout-dialog-container.component.ts
@@ -1,5 +1,5 @@
 import { CommonModule } from "@angular/common";
-import { Component, input, OnInit } from "@angular/core";
+import { Component, effect, inject, input, signal, ChangeDetectionStrategy } from "@angular/core";
 
 import { JslibModule } from "@bitwarden/angular/jslib.module";
 import { SendType } from "@bitwarden/common/tools/send/enums/send-type";
@@ -10,32 +10,39 @@ import { FilePopoutUtilsService } from "../../services/file-popout-utils.service
 
 import { SendFilePopoutDialogComponent } from "./send-file-popout-dialog.component";
 
-// FIXME(https://bitwarden.atlassian.net/browse/CL-764): Migrate to OnPush
-// eslint-disable-next-line @angular-eslint/prefer-on-push-component-change-detection
 @Component({
+  changeDetection: ChangeDetectionStrategy.OnPush,
   selector: "send-file-popout-dialog-container",
   templateUrl: "./send-file-popout-dialog-container.component.html",
   imports: [JslibModule, CommonModule],
 })
-export class SendFilePopoutDialogContainerComponent implements OnInit {
-  // FIXME(https://bitwarden.atlassian.net/browse/CL-903): Migrate to Signals
-  // eslint-disable-next-line @angular-eslint/prefer-signals
-  config = input.required<SendFormConfig>();
-
-  constructor(
-    private dialogService: DialogService,
-    private filePopoutUtilsService: FilePopoutUtilsService,
-  ) {}
-
-  ngOnInit() {
-    if (
-      this.config().sendType === SendType.File &&
-      this.config().mode === "add" &&
-      this.filePopoutUtilsService.showFilePopoutMessage(window)
-    ) {
-      this.dialogService.open(SendFilePopoutDialogComponent, {
-        positionStrategy: new CenterPositionStrategy(),
-      });
-    }
+export class SendFilePopoutDialogContainerComponent {
+  private readonly dialogService = inject(DialogService);
+  private readonly filePopoutUtilsService = inject(FilePopoutUtilsService);
+
+  readonly config = input.required<SendFormConfig>();
+
+  /**
+   * Tracks if the dialog has already been opened. This prevents multiple dialogs from opening if config is updated.
+   */
+  private readonly dialogOpened = signal(false);
+
+  constructor() {
+    effect(() => {
+      if (this.dialogOpened()) {
+        return;
+      }
+
+      if (
+        this.config().sendType === SendType.File &&
+        this.config().mode === "add" &&
+        this.filePopoutUtilsService.showFilePopoutMessage(window)
+      ) {
+        this.dialogService.open(SendFilePopoutDialogComponent, {
+          positionStrategy: new CenterPositionStrategy(),
+        });
+        this.dialogOpened.set(true);
+      }
+    });
   }
 }
diff --git a/apps/browser/src/tools/popup/send-v2/send-file-popout-dialog/send-file-popout-dialog.component.ts b/apps/browser/src/tools/popup/send-v2/send-file-popout-dialog/send-file-popout-dialog.component.ts
index 23fa744995aa..0406ad76cadb 100644
--- a/apps/browser/src/tools/popup/send-v2/send-file-popout-dialog/send-file-popout-dialog.component.ts
+++ b/apps/browser/src/tools/popup/send-v2/send-file-popout-dialog/send-file-popout-dialog.component.ts
@@ -1,5 +1,6 @@
 import { CommonModule } from "@angular/common";
 import { Component } from "@angular/core";
+import { Router } from "@angular/router";
 
 import { JslibModule } from "@bitwarden/angular/jslib.module";
 import { ButtonModule, DialogModule, DialogService, TypographyModule } from "@bitwarden/components";
@@ -14,13 +15,18 @@ import BrowserPopupUtils from "../../../../platform/browser/browser-popup-utils"
   imports: [JslibModule, CommonModule, DialogModule, ButtonModule, TypographyModule],
 })
 export class SendFilePopoutDialogComponent {
-  constructor(private dialogService: DialogService) {}
+  constructor(
+    private dialogService: DialogService,
+    private router: Router,
+  ) {}
 
   async popOutWindow() {
     await BrowserPopupUtils.openCurrentPagePopout(window);
   }
 
-  close() {
+  // If the user selects "cancel" when presented the dialog, navigate back to the main Send tab
+  async close() {
     this.dialogService.closeAll();
+    await this.router.navigate(["/tabs/send"]);
   }
 }
diff --git a/apps/browser/src/tools/popup/settings/import/import-browser-v2.component.html b/apps/browser/src/tools/popup/settings/import/import-browser-v2.component.html
index 5458b46535a1..180b7988ee5a 100644
--- a/apps/browser/src/tools/popup/settings/import/import-browser-v2.component.html
+++ b/apps/browser/src/tools/popup/settings/import/import-browser-v2.component.html
@@ -12,6 +12,8 @@
   >
   </tools-import>
 
+  <import-file-popout-dialog-container></import-file-popout-dialog-container>
+
   <popup-footer slot="footer">
     <button
       [disabled]="disabled"
diff --git a/apps/browser/src/tools/popup/settings/import/import-browser-v2.component.ts b/apps/browser/src/tools/popup/settings/import/import-browser-v2.component.ts
index a88cc3f81dc8..0bbcd61c3a07 100644
--- a/apps/browser/src/tools/popup/settings/import/import-browser-v2.component.ts
+++ b/apps/browser/src/tools/popup/settings/import/import-browser-v2.component.ts
@@ -20,6 +20,8 @@ import { PopupFooterComponent } from "../../../../platform/popup/layout/popup-fo
 import { PopupHeaderComponent } from "../../../../platform/popup/layout/popup-header.component";
 import { PopupPageComponent } from "../../../../platform/popup/layout/popup-page.component";
 
+import { ImportFilePopoutDialogContainerComponent } from "./import-file-popout-dialog-container.component";
+
 // FIXME(https://bitwarden.atlassian.net/browse/CL-764): Migrate to OnPush
 // eslint-disable-next-line @angular-eslint/prefer-on-push-component-change-detection
 @Component({
@@ -35,6 +37,7 @@ import { PopupPageComponent } from "../../../../platform/popup/layout/popup-page
     PopupFooterComponent,
     PopupHeaderComponent,
     PopOutComponent,
+    ImportFilePopoutDialogContainerComponent,
   ],
   providers: [
     ...ImporterProviders,
diff --git a/apps/browser/src/tools/popup/settings/import/import-file-popout-dialog-container.component.ts b/apps/browser/src/tools/popup/settings/import/import-file-popout-dialog-container.component.ts
new file mode 100644
index 000000000000..8711aaab76c6
--- /dev/null
+++ b/apps/browser/src/tools/popup/settings/import/import-file-popout-dialog-container.component.ts
@@ -0,0 +1,34 @@
+import { CommonModule } from "@angular/common";
+import { Component, OnInit, ChangeDetectionStrategy, OnDestroy } from "@angular/core";
+
+import { JslibModule } from "@bitwarden/angular/jslib.module";
+import { DialogRef, DialogService } from "@bitwarden/components";
+
+import { FilePopoutUtilsService } from "../../services/file-popout-utils.service";
+
+import { ImportFilePopoutDialogComponent } from "./import-file-popout-dialog.component";
+
+@Component({
+  changeDetection: ChangeDetectionStrategy.OnPush,
+  selector: "import-file-popout-dialog-container",
+  template: "",
+  imports: [JslibModule, CommonModule],
+})
+export class ImportFilePopoutDialogContainerComponent implements OnInit, OnDestroy {
+  private dialogRef?: DialogRef;
+
+  constructor(
+    private dialogService: DialogService,
+    private filePopoutUtilsService: FilePopoutUtilsService,
+  ) {}
+
+  ngOnInit() {
+    if (this.filePopoutUtilsService.showFilePopoutMessage(window)) {
+      this.dialogRef = this.dialogService.open(ImportFilePopoutDialogComponent);
+    }
+  }
+
+  ngOnDestroy() {
+    this.dialogRef?.close();
+  }
+}
diff --git a/apps/browser/src/tools/popup/settings/import/import-file-popout-dialog.component.html b/apps/browser/src/tools/popup/settings/import/import-file-popout-dialog.component.html
new file mode 100644
index 000000000000..d8d43adc5194
--- /dev/null
+++ b/apps/browser/src/tools/popup/settings/import/import-file-popout-dialog.component.html
@@ -0,0 +1,18 @@
+<bit-simple-dialog dialogSize="default">
+  <i bitDialogIcon class="bwi bwi-info-circle tw-text-info tw-text-3xl" aria-hidden="true"></i>
+  <ng-container bitDialogContent>
+    <div bitTypography="h3">
+      {{ "sendFilePopoutDialogText" | i18n }}
+    </div>
+    <div bitTypography="body1">{{ "importPopoutDialogDesc" | i18n }}</div>
+  </ng-container>
+  <ng-container bitDialogFooter>
+    <button buttonType="primary" bitButton type="button" (click)="popOutWindow()">
+      {{ "popOut" | i18n }}
+      <i class="bwi bwi-popout tw-ml-1" aria-hidden="true"></i>
+    </button>
+    <button bitButton buttonType="secondary" type="button" (click)="close()">
+      {{ "cancel" | i18n }}
+    </button>
+  </ng-container>
+</bit-simple-dialog>
diff --git a/apps/browser/src/tools/popup/settings/import/import-file-popout-dialog.component.ts b/apps/browser/src/tools/popup/settings/import/import-file-popout-dialog.component.ts
new file mode 100644
index 000000000000..6ba2c9df3d27
--- /dev/null
+++ b/apps/browser/src/tools/popup/settings/import/import-file-popout-dialog.component.ts
@@ -0,0 +1,31 @@
+import { CommonModule } from "@angular/common";
+import { Component, ChangeDetectionStrategy } from "@angular/core";
+
+import { JslibModule } from "@bitwarden/angular/jslib.module";
+import { ButtonModule, DialogModule, DialogService, TypographyModule } from "@bitwarden/components";
+
+import BrowserPopupUtils from "../../../../platform/browser/browser-popup-utils";
+import { PopupRouterCacheService } from "../../../../platform/popup/view-cache/popup-router-cache.service";
+
+@Component({
+  changeDetection: ChangeDetectionStrategy.OnPush,
+  selector: "import-file-popout-dialog",
+  templateUrl: "./import-file-popout-dialog.component.html",
+  imports: [JslibModule, CommonModule, DialogModule, ButtonModule, TypographyModule],
+})
+export class ImportFilePopoutDialogComponent {
+  constructor(
+    private dialogService: DialogService,
+    private popupRouterCacheService: PopupRouterCacheService,
+  ) {}
+
+  async popOutWindow() {
+    await BrowserPopupUtils.openCurrentPagePopout(window);
+  }
+
+  // If the user selects "cancel" when presented the dialog, navigate back to the main Send tab
+  async close() {
+    this.dialogService.closeAll();
+    await this.popupRouterCacheService.back();
+  }
+}
diff --git a/apps/browser/src/vault/popup/settings/vault-settings-v2.component.ts b/apps/browser/src/vault/popup/settings/vault-settings-v2.component.ts
index ff6e9b4065c3..1bd1baf26d76 100644
--- a/apps/browser/src/vault/popup/settings/vault-settings-v2.component.ts
+++ b/apps/browser/src/vault/popup/settings/vault-settings-v2.component.ts
@@ -13,8 +13,6 @@ import { CipherArchiveService } from "@bitwarden/common/vault/abstractions/ciphe
 import { SyncService } from "@bitwarden/common/vault/abstractions/sync/sync.service.abstraction";
 import { BadgeComponent, ItemModule, ToastOptions, ToastService } from "@bitwarden/components";
 
-import { BrowserApi } from "../../../platform/browser/browser-api";
-import BrowserPopupUtils from "../../../platform/browser/browser-popup-utils";
 import { PopOutComponent } from "../../../platform/popup/components/pop-out.component";
 import { PopupHeaderComponent } from "../../../platform/popup/layout/popup-header.component";
 import { PopupPageComponent } from "../../../platform/popup/layout/popup-page.component";
@@ -77,9 +75,6 @@ export class VaultSettingsV2Component implements OnInit, OnDestroy {
 
   async import() {
     await this.router.navigate(["/import"]);
-    if (await BrowserApi.isPopupOpen()) {
-      await BrowserPopupUtils.openCurrentPagePopout(window);
-    }
   }
 
   async sync() {