diff --git a/apps/web/src/app/vault/components/vault-item-dialog/vault-item-dialog.component.ts b/apps/web/src/app/vault/components/vault-item-dialog/vault-item-dialog.component.ts
index 4969ea2b16..d3d0703605 100644
--- a/apps/web/src/app/vault/components/vault-item-dialog/vault-item-dialog.component.ts
+++ b/apps/web/src/app/vault/components/vault-item-dialog/vault-item-dialog.component.ts
@@ -207,6 +207,7 @@ export class VaultItemDialogComponent implements OnInit, OnDestroy {
     private accountService: AccountService,
     private router: Router,
     private billingAccountProfileStateService: BillingAccountProfileStateService,
+    private premiumUpgradeService: PremiumUpgradePromptService,
   ) {
     this.updateTitle();
   }
@@ -297,6 +298,13 @@ export class VaultItemDialogComponent implements OnInit, OnDestroy {
   };
 
   openAttachmentsDialog = async () => {
+    const canAccessAttachments = await firstValueFrom(this.canAccessAttachments$);
+
+    if (!canAccessAttachments) {
+      await this.premiumUpgradeService.promptForPremium();
+      return;
+    }
+
     const dialogRef = this.dialogService.open<AttachmentDialogCloseResult, { cipherId: CipherId }>(
       AttachmentsV2Component,
       {
diff --git a/apps/web/src/app/vault/individual-vault/vault.component.ts b/apps/web/src/app/vault/individual-vault/vault.component.ts
index 734ab5acf1..aac686f21a 100644
--- a/apps/web/src/app/vault/individual-vault/vault.component.ts
+++ b/apps/web/src/app/vault/individual-vault/vault.component.ts
@@ -611,6 +611,12 @@ export class VaultComponent implements OnInit, OnDestroy {
     const result = await lastValueFrom(this.vaultItemDialogRef.closed);
     this.vaultItemDialogRef = undefined;
 
+    // When the dialog is closed for a premium upgrade, return early as the user
+    // should be navigated to the subscription settings elsewhere
+    if (result === VaultItemDialogResult.PremiumUpgrade) {
+      return;
+    }
+
     // If the dialog was closed by deleting the cipher, refresh the vault.
     if (result === VaultItemDialogResult.Deleted || result === VaultItemDialogResult.Saved) {
       this.refresh();