diff --git a/app/common/src/text/english.json b/app/common/src/text/english.json
index a89c0135bc24d..32e6d5d1bb5d4 100644
--- a/app/common/src/text/english.json
+++ b/app/common/src/text/english.json
@@ -400,6 +400,7 @@
   "thisFolderFailedToFetch": "This folder failed to fetch.",
   "yourTrashIsEmpty": "Your trash is empty.",
   "deleteTheAssetTypeTitle": "delete the $0 '$1'",
+  "deleteTheAssetTypeTitleForever": "permanently delete the $0 '$1'",
   "trashTheAssetTypeTitle": "move the $0 '$1' to Trash",
   "notImplemetedYet": "Not implemented yet.",
   "newLabelButtonLabel": "New label",
@@ -445,7 +446,8 @@
   "youHaveNoRecentProjects": "You have no recent projects. Switch to another category to create a project.",
   "youHaveNoFiles": "This folder is empty. You can create a project using the buttons above.",
   "placeholderChatPrompt": "Login or register to access live chat with our support team.",
-  "confirmPrompt": "Are you sure you want to $0?",
+  "confirmPrompt": "Do you really want to $0?",
+  "confirmPromptCannotUndo": "Do you really want to $0? This operation is final and cannot be undone.",
   "couldNotInviteUser": "Could not invite user $0",
   "inviteFormSeatsLeft": "You have $0 seats left on your plan. Upgrade to invite more",
   "inviteFormSeatsLeftError": "You have exceed the number of seats on your plan by $0",
diff --git a/app/common/src/text/index.ts b/app/common/src/text/index.ts
index 8c532137d50e2..1a3eb3d03354e 100644
--- a/app/common/src/text/index.ts
+++ b/app/common/src/text/index.ts
@@ -43,8 +43,10 @@ interface PlaceholderOverrides {
   readonly deleteUserGroupActionText: [groupName: string]
   readonly removeUserFromUserGroupActionText: [userName: string, groupName: string]
   readonly confirmPrompt: [action: string]
+  readonly confirmPromptCannotUndo: [action: string]
   readonly trashTheAssetTypeTitle: [assetType: string, assetName: string]
   readonly deleteTheAssetTypeTitle: [assetType: string, assetName: string]
+  readonly deleteTheAssetTypeTitleForever: [assetType: string, assetName: string]
   readonly couldNotInviteUser: [userEmail: string]
   readonly filesWithoutConflicts: [fileCount: number]
   readonly projectsWithoutConflicts: [projectCount: number]
diff --git a/app/gui/src/dashboard/layouts/AssetContextMenu.tsx b/app/gui/src/dashboard/layouts/AssetContextMenu.tsx
index 440ac70788e35..753fb7bbb945e 100644
--- a/app/gui/src/dashboard/layouts/AssetContextMenu.tsx
+++ b/app/gui/src/dashboard/layouts/AssetContextMenu.tsx
@@ -209,7 +209,8 @@ export default function AssetContextMenu(props: AssetContextMenuProps) {
               setModal(
                 <ConfirmDeleteModal
                   defaultOpen
-                  actionText={`delete the ${asset.type} '${asset.title}' forever`}
+                  cannotUndo
+                  actionText={getText('deleteTheAssetTypeTitleForever', asset.type, asset.title)}
                   doDelete={() => {
                     const ids = new Set([asset.id])
                     dispatchAssetEvent({ type: AssetEventType.deleteForever, ids })
diff --git a/app/gui/src/dashboard/layouts/AssetsTableContextMenu.tsx b/app/gui/src/dashboard/layouts/AssetsTableContextMenu.tsx
index 09c5496f9bd5c..b0f43adfd3134 100644
--- a/app/gui/src/dashboard/layouts/AssetsTableContextMenu.tsx
+++ b/app/gui/src/dashboard/layouts/AssetsTableContextMenu.tsx
@@ -155,7 +155,7 @@ export default function AssetsTableContextMenu(props: AssetsTableContextMenuProp
 
   if (category.type === 'trash') {
     return (
-      selectedKeys.size !== 0 && (
+      selectedKeys.size > 1 && (
         <ContextMenu
           aria-label={getText('assetsTableContextMenuLabel')}
           hidden={hidden}
diff --git a/app/gui/src/dashboard/modals/ConfirmDeleteModal.tsx b/app/gui/src/dashboard/modals/ConfirmDeleteModal.tsx
index b3416db7fd423..f03a8c560ead7 100644
--- a/app/gui/src/dashboard/modals/ConfirmDeleteModal.tsx
+++ b/app/gui/src/dashboard/modals/ConfirmDeleteModal.tsx
@@ -11,29 +11,36 @@ import { useText } from '#/providers/TextProvider'
 
 /** Props for a {@link ConfirmDeleteModal}. */
 export interface ConfirmDeleteModalProps {
-  readonly defaultOpen?: boolean
+  readonly defaultOpen?: boolean | undefined
+  readonly cannotUndo?: boolean | undefined
   /** Must fit in the sentence "Are you sure you want to <action>?". */
   readonly actionText: string
   /** The label shown on the colored confirmation button. "Delete" by default. */
-  readonly actionButtonLabel?: string
+  readonly actionButtonLabel?: string | undefined
   readonly doDelete: () => void
 }
 
 /** A modal for confirming the deletion of an asset. */
 export default function ConfirmDeleteModal(props: ConfirmDeleteModalProps) {
-  const { defaultOpen, actionText, actionButtonLabel = 'Delete', doDelete } = props
+  const {
+    defaultOpen = false,
+    cannotUndo = false,
+    actionText,
+    actionButtonLabel = 'Delete',
+    doDelete,
+  } = props
 
   const { unsetModal } = useSetModal()
   const { getText } = useText()
 
+  console.log('hello owo', cannotUndo)
+
   return (
-    <Dialog
-      title={getText('areYouSure')}
-      role="alertdialog"
-      modalProps={defaultOpen == null ? {} : { defaultOpen }}
-    >
+    <Dialog title={getText('areYouSure')} role="alertdialog" modalProps={{ defaultOpen }}>
       <Form schema={z.object({})} method="dialog" onSubmit={doDelete} onSubmitSuccess={unsetModal}>
-        <Text className="relative">{getText('confirmPrompt', actionText)}</Text>
+        <Text className="relative">
+          {getText(cannotUndo ? 'confirmPromptCannotUndo' : 'confirmPrompt', actionText)}
+        </Text>
 
         <ButtonGroup>
           <Form.Submit variant="delete" className="relative">