diff --git a/src/app/send/add-edit.component.html b/src/app/send/add-edit.component.html
index 64b0177b..7e504786 100644
--- a/src/app/send/add-edit.component.html
+++ b/src/app/send/add-edit.component.html
@@ -10,7 +10,8 @@
             </div>
             <div class="modal-body" *ngIf="send">
                 <app-callout *ngIf="disableSend">
-                    <span>{{'sendDisabledWarning' | i18n}}</span>
+                    <span>{{(send.hideEmail && editMode && disableAnonymousSend ?
+                        'anonymousSendDisabledWarning' : 'sendDisabledWarning') | i18n}}</span>
                 </app-callout>
                 <div class="row">
                     <div class="col-6 form-group">
@@ -212,7 +213,7 @@
                             <input class="form-check-input" type="checkbox" [(ngModel)]="send.hideEmail" id="hideEmail" 
                             name="HideEmail" [disabled]="disableAnonymousSend || disableSend">
                             <label class="form-check-label" for="hideEmail">
-                                {{'hideEmail' | i18n}}<span *ngIf="disableAnonymousSend" class="font-italic"> {{'anonymousSendDisabled' | i18n}}</span>
+                                {{'hideEmail' | i18n}}<span *ngIf="disableAnonymousSend && !editMode" class="font-italic"> {{'anonymousSendDisabled' | i18n}}</span>
                             </label>
                         </div>
                     </div>
diff --git a/src/locales/en/messages.json b/src/locales/en/messages.json
index 7927e1fb..6b7f73b3 100644
--- a/src/locales/en/messages.json
+++ b/src/locales/en/messages.json
@@ -3647,6 +3647,10 @@
     "message": "Due to an enterprise policy, you are only able to delete an existing Send.",
     "description": "'Send' is a noun and the name of a feature called 'Bitwarden Send'. It should not be translated."
   },
+  "anonymousSendDisabledWarning": {
+    "message": "Due to an enterprise policy, you are only able to delete an existing Send that hides your email address. There are no restrictions on Sends that do not hide your email address.",
+    "description": "'Send' is a noun and the name of a feature called 'Bitwarden Send'. It should not be translated."
+  },
   "modifiedPolicyId": {
     "message": "Modified policy $ID$.",
     "placeholders": {