diff --git a/src/app/settings/change-password.component.html b/src/app/settings/change-password.component.html
index c172141f23e..092e5bcba5e 100644
--- a/src/app/settings/change-password.component.html
+++ b/src/app/settings/change-password.component.html
@@ -29,7 +29,7 @@
     <div class="form-group">
         <div class="form-check">
             <input class="form-check-input" type="checkbox" id="rotateEncKey" name="RotateEncKey" [(ngModel)]="rotateEncKey"
-                (change)="showEncKeyWarning()">
+                (change)="rotateEncKeyClicked()">
             <label class="form-check-label" for="rotateEncKey">
                 {{'rotateAccountEncKey' | i18n}}
             </label>
diff --git a/src/app/settings/change-password.component.ts b/src/app/settings/change-password.component.ts
index 7023af5de75..c48516407ba 100644
--- a/src/app/settings/change-password.component.ts
+++ b/src/app/settings/change-password.component.ts
@@ -128,8 +128,30 @@ export class ChangePasswordComponent implements OnInit {
         }, 300);
     }
 
-    async showEncKeyWarning() {
+    async rotateEncKeyClicked() {
         if (this.rotateEncKey) {
+            const ciphers = await this.cipherService.getAllDecrypted();
+            let hasOldAttachments = false;
+            if (ciphers != null) {
+                for (let i = 0; i < ciphers.length; i++) {
+                    if (ciphers[i].organizationId == null && ciphers[i].hasOldAttachments) {
+                        hasOldAttachments = true;
+                        break;
+                    }
+                }
+            }
+
+            if (hasOldAttachments) {
+                const learnMore = await this.platformUtilsService.showDialog(
+                    this.i18nService.t('oldAttachmentsNeedFixDesc'), null,
+                    this.i18nService.t('learnMore'), this.i18nService.t('close'), 'warning');
+                if (learnMore) {
+                    this.platformUtilsService.launchUri('https://help.bitwarden.com/article/attachments/');
+                }
+                this.rotateEncKey = false;
+                return;
+            }
+
             const result = await this.platformUtilsService.showDialog(
                 this.i18nService.t('updateEncryptionKeyWarning') + ' ' +
                 this.i18nService.t('rotateEncKeyConfirmation'), this.i18nService.t('rotateEncKeyTitle'),
diff --git a/src/locales/en/messages.json b/src/locales/en/messages.json
index c3008b30c9d..94a5c751b0c 100644
--- a/src/locales/en/messages.json
+++ b/src/locales/en/messages.json
@@ -2541,12 +2541,15 @@
     "message": "Are you sure you want to rotate your account's encryption key?"
   },
   "attachmentsNeedFix": {
-    "message": "This item has old attachments that need to be fixed."
+    "message": "This item has old file attachments that need to be fixed."
   },
   "attachmentFixDesc": {
-    "message": "This is an old attachment the needs to be fixed. Click to learn more."
+    "message": "This is an old file attachment the needs to be fixed. Click to learn more."
   },
   "fix": {
     "message": "Fix"
+  },
+  "oldAttachmentsNeedFixDesc": {
+    "message": "There are old file attachments in your vault that need to be fixed before you can rotate your account's encryption key."
   }
 }