diff --git a/app/actions/definitions/documents.tsx b/app/actions/definitions/documents.tsx
index 091903661f..57c7990151 100644
--- a/app/actions/definitions/documents.tsx
+++ b/app/actions/definitions/documents.tsx
@@ -81,6 +81,7 @@ import {
   trashPath,
   documentEditPath,
 } from "~/utils/routeHelpers";
+import { documentBreadcrumbText } from "~/components/DocumentBreadcrumb";
 import CollectionIcon from "~/components/Icons/CollectionIcon";
 import type {
   Action,
@@ -108,19 +109,21 @@ export const openDocument = createActionWithChildren({
   shortcut: ["o", "d"],
   keywords: "go to",
   icon: <DocumentIcon />,
-  children: ({ stores }) => {
+  children: ({ stores, t }) => {
     const nodes = stores.collections.navigationNodes.reduce(
       (acc, node) => [...acc, ...node.children],
       [] as NavigationNode[]
     );
     const documents = stores.documents.orderedData;
 
-    return uniqBy([...documents, ...nodes], "id").map((item) =>
-      createInternalLinkAction({
+    return uniqBy([...documents, ...nodes], "id").map((item) => {
+      const document = stores.documents.get(item.id);
+      return createInternalLinkAction({
         // Note: using url which includes the slug rather than id here to bust
         // cache if the document is renamed
         id: item.url,
         name: item.title,
+        description: document ? documentBreadcrumbText(document, t) : undefined,
         icon: item.icon ? (
           <Icon
             value={item.icon}
@@ -132,8 +135,8 @@ export const openDocument = createActionWithChildren({
         ),
         section: DocumentSection,
         to: item.url,
-      })
-    );
+      });
+    });
   },
 });
 
diff --git a/app/components/CommandBar/useRecentDocumentActions.tsx b/app/components/CommandBar/useRecentDocumentActions.tsx
index a104350439..bb109fc0fd 100644
--- a/app/components/CommandBar/useRecentDocumentActions.tsx
+++ b/app/components/CommandBar/useRecentDocumentActions.tsx
@@ -1,13 +1,16 @@
 import { DocumentIcon } from "outline-icons";
 import { useMemo } from "react";
+import { useTranslation } from "react-i18next";
 import Icon from "@shared/components/Icon";
 import { createInternalLinkAction } from "~/actions";
 import { RecentSection } from "~/actions/sections";
+import { documentBreadcrumbText } from "~/components/DocumentBreadcrumb";
 import useStores from "~/hooks/useStores";
 import { documentPath } from "~/utils/routeHelpers";
 
 const useRecentDocumentActions = (count = 6) => {
   const { documents, ui } = useStores();
+  const { t } = useTranslation();
 
   return useMemo(
     () =>
@@ -19,6 +22,7 @@ const useRecentDocumentActions = (count = 6) => {
             name: item.titleWithDefault,
             analyticsName: "Recently viewed document",
             section: RecentSection,
+            description: documentBreadcrumbText(item, t),
             icon: item.icon ? (
               <Icon
                 value={item.icon}
@@ -31,7 +35,7 @@ const useRecentDocumentActions = (count = 6) => {
             to: documentPath(item),
           })
         ),
-    [count, ui.activeDocumentId, documents.recentlyViewed]
+    [count, ui.activeDocumentId, documents.recentlyViewed, t]
   );
 };
 
diff --git a/app/components/DocumentBreadcrumb.tsx b/app/components/DocumentBreadcrumb.tsx
index c3da07a972..aa53d86efc 100644
--- a/app/components/DocumentBreadcrumb.tsx
+++ b/app/components/DocumentBreadcrumb.tsx
@@ -1,10 +1,10 @@
+import type { TFunction } from "i18next";
 import { observer } from "mobx-react";
 import { ArchiveIcon, GoToIcon, TrashIcon } from "outline-icons";
 import * as React from "react";
 import { useTranslation } from "react-i18next";
 import styled from "styled-components";
 import Icon from "@shared/components/Icon";
-import type { NavigationNode } from "@shared/types";
 import type Collection from "~/models/Collection";
 import type Document from "~/models/Document";
 import Breadcrumb from "~/components/Breadcrumb";
@@ -20,6 +20,56 @@ import { archivePath, trashPath } from "~/utils/routeHelpers";
 import { createInternalLinkAction } from "~/actions";
 import { ActiveDocumentSection } from "~/actions/sections";
 
+/**
+ * Returns the breadcrumb parts leading up to a document, separating the
+ * (possibly deleted) collection label from ancestor document titles. The
+ * document itself is not included.
+ *
+ * @param document - the document to compute the breadcrumb for.
+ * @param t - translation function for fallback titles.
+ * @returns the collection label and ancestor titles.
+ */
+export function documentBreadcrumbParts(
+  document: Document,
+  t: TFunction
+): { collection: string | undefined; ancestors: string[] } {
+  let collectionLabel: string | undefined;
+  if (document.isCollectionDeleted) {
+    collectionLabel = t("Deleted Collection");
+  } else if (document.collection?.name) {
+    collectionLabel = document.collection.name;
+  }
+
+  return {
+    collection: collectionLabel,
+    ancestors: document.pathTo
+      .slice(0, -1)
+      .map((node) => node.title || t("Untitled")),
+  };
+}
+
+/**
+ * Returns the breadcrumb path leading up to a document as a plain text
+ * string. Includes the collection name (or "Deleted Collection" fallback)
+ * and any ancestor document titles, slash-separated.
+ *
+ * @param document - the document to compute the breadcrumb for.
+ * @param t - translation function for fallback titles.
+ * @returns the breadcrumb as a slash-separated string, or undefined if the
+ * document has no resolvable parent context.
+ */
+export function documentBreadcrumbText(
+  document: Document,
+  t: TFunction
+): string | undefined {
+  const parts = documentBreadcrumbParts(document, t);
+  const segments = [
+    ...(parts.collection ? [parts.collection] : []),
+    ...parts.ancestors,
+  ];
+  return segments.length ? segments.join(" / ") : undefined;
+}
+
 type Props = {
   children?: React.ReactNode;
   document: Document;
@@ -147,22 +197,25 @@ function DocumentBreadcrumb(
       return <></>;
     }
 
-    const slicedPath = reverse
-      ? path.slice(depth && -depth)
-      : path.slice(0, depth);
+    const { collection: collectionLabel, ancestors: ancestorLabels } =
+      documentBreadcrumbParts(document, t);
+
+    const slicedAncestors = reverse
+      ? ancestorLabels.slice(depth && -depth)
+      : ancestorLabels.slice(0, depth);
 
     const showCollection =
-      collection &&
-      (!reverse || depth === undefined || slicedPath.length < depth);
+      !!collectionLabel &&
+      (!reverse || depth === undefined || slicedAncestors.length < depth);
 
     return (
       <>
-        {showCollection && collection.name}
-        {slicedPath.map((node: NavigationNode, index: number) => (
-          <React.Fragment key={node.id}>
+        {showCollection && collectionLabel}
+        {slicedAncestors.map((label, index) => (
+          <React.Fragment key={index}>
             {showCollection && <SmallSlash />}
-            {node.title || t("Untitled")}
-            {!showCollection && index !== slicedPath.length - 1 && (
+            {label}
+            {!showCollection && index !== slicedAncestors.length - 1 && (
               <SmallSlash />
             )}
           </React.Fragment>