diff --git a/apps/browser/src/_locales/en/messages.json b/apps/browser/src/_locales/en/messages.json
index bf1eedd826..fe5400c6a9 100644
--- a/apps/browser/src/_locales/en/messages.json
+++ b/apps/browser/src/_locales/en/messages.json
@@ -2406,5 +2406,17 @@
   "toggleCollapse": {
     "message": "Toggle collapse",
     "description": "Toggling an expand/collapse state."
+  },
+  "passwordRepromptDisabledAutofillOnPageLoad": {
+    "message": "Items with master password re-prompt cannot be auto-filled on page load. Auto-fill on page load turned off.",
+    "description": "Toast message for describing that master password re-prompt cannot be auto-filled on page load."
+  },
+  "autofillOnPageLoadSetToDefault": {
+    "message": "Auto-fill on page load set to use default setting.",
+    "description": "Toast message for informing the user that auto-fill on page load has been set to the default setting."
+  },
+  "turnOffMasterPasswordPromptToEditField": {
+    "message": "Turn off master password re-prompt to edit this field",
+    "description": "Message appearing below the autofill on load message when master password reprompt is set for a vault item."
   }
 }
diff --git a/apps/browser/src/autofill/services/autofill.service.ts b/apps/browser/src/autofill/services/autofill.service.ts
index fcf4dffd4a..c494b8ece0 100644
--- a/apps/browser/src/autofill/services/autofill.service.ts
+++ b/apps/browser/src/autofill/services/autofill.service.ts
@@ -19,9 +19,9 @@ import AutofillScript from "../models/autofill-script";
 import {
   AutoFillOptions,
   AutofillService as AutofillServiceInterface,
-  PageDetail,
   FormData,
   GenerateFillScriptOptions,
+  PageDetail,
 } from "./abstractions/autofill.service";
 import {
   AutoFillConstants,
@@ -260,7 +260,7 @@ export default class AutofillService implements AutofillServiceInterface {
       }
     }
 
-    if (cipher == null) {
+    if (cipher == null || (cipher.reprompt === CipherRepromptType.Password && !fromCommand)) {
       return null;
     }
 
diff --git a/apps/browser/src/vault/popup/components/vault/add-edit.component.html b/apps/browser/src/vault/popup/components/vault/add-edit.component.html
index 1373669ca1..dda71cb0d6 100644
--- a/apps/browser/src/vault/popup/components/vault/add-edit.component.html
+++ b/apps/browser/src/vault/popup/components/vault/add-edit.component.html
@@ -564,6 +564,7 @@
           <select
             id="autofillOnPageLoad"
             name="AutofillOnPageLoad"
+            [disabled]="reprompt"
             [(ngModel)]="cipher.login.autofillOnPageLoad"
           >
             <option *ngFor="let o of autofillOnPageLoadOptions" [ngValue]="o.value">
@@ -572,6 +573,9 @@
           </select>
         </div>
       </div>
+      <div class="box-footer !tw-mb-0 !tw-pb-0" *ngIf="reprompt">
+        {{ "turnOffMasterPasswordPromptToEditField" | i18n }}
+      </div>
     </div>
     <div class="box">
       <div class="box-content">
diff --git a/apps/browser/src/vault/popup/components/vault/add-edit.component.ts b/apps/browser/src/vault/popup/components/vault/add-edit.component.ts
index 6148e31dd6..54cb08ae89 100644
--- a/apps/browser/src/vault/popup/components/vault/add-edit.component.ts
+++ b/apps/browser/src/vault/popup/components/vault/add-edit.component.ts
@@ -264,4 +264,27 @@ export class AddEditComponent extends BaseAddEditComponent {
       }
     }, 200);
   }
+
+  repromptChanged() {
+    super.repromptChanged();
+
+    if (!this.showAutoFillOnPageLoadOptions) {
+      return;
+    }
+
+    if (this.reprompt) {
+      this.platformUtilsService.showToast(
+        "info",
+        null,
+        this.i18nService.t("passwordRepromptDisabledAutofillOnPageLoad")
+      );
+      return;
+    }
+
+    this.platformUtilsService.showToast(
+      "info",
+      null,
+      this.i18nService.t("autofillOnPageLoadSetToDefault")
+    );
+  }
 }
diff --git a/libs/angular/src/vault/components/add-edit.component.ts b/libs/angular/src/vault/components/add-edit.component.ts
index 6bcd72082b..377fe88b63 100644
--- a/libs/angular/src/vault/components/add-edit.component.ts
+++ b/libs/angular/src/vault/components/add-edit.component.ts
@@ -272,6 +272,9 @@ export class AddEditComponent implements OnInit, OnDestroy {
     }
     this.previousCipherId = this.cipherId;
     this.reprompt = this.cipher.reprompt !== CipherRepromptType.None;
+    if (this.reprompt) {
+      this.cipher.login.autofillOnPageLoad = this.autofillOnPageLoadOptions[2].value;
+    }
   }
 
   async submit(): Promise<boolean> {
@@ -570,8 +573,10 @@ export class AddEditComponent implements OnInit, OnDestroy {
     this.reprompt = !this.reprompt;
     if (this.reprompt) {
       this.cipher.reprompt = CipherRepromptType.Password;
+      this.cipher.login.autofillOnPageLoad = this.autofillOnPageLoadOptions[2].value;
     } else {
       this.cipher.reprompt = CipherRepromptType.None;
+      this.cipher.login.autofillOnPageLoad = this.autofillOnPageLoadOptions[0].value;
     }
   }