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You know you worked out the deployment plan with an AI a few weeks back, but which chat was it in? And did that detail end up in a memory or a file? Ask is the one tool in the dashboard that answers natural-language questions about everything you have stored in MemoryPlugin. You type a question, it searches the source you point it at, and it writes back an answer with links to the originals so you can check its work.
Ask is a single interface with three modes. It is not the same as the Ask entry inside the Chat History section, which only ever searches your imported chats. This page covers the unified Ask tool, which can switch between chat history, memories, and files in one place. Open it from the sidebar or press ⇧⌘O / Shift+Ctrl+O.
The Ask interface with History, Files, and Memories mode pills, a question about the launch date, and a streamed answer citing three source conversations

The three modes

A pill toggle at the bottom of the composer switches Ask between three sources:
ModeSearchesUse it to
HistoryYour imported and synced AI conversationsFind past decisions, project context, or how you discussed something before
FilesDocuments in your file bucketsPull answers out of PDFs, Word docs, Markdown, and text files
MemoriesMemories in your memory bucketsRecall preferences, facts, and notes you have saved
The pills read History, Files, and Memories. Once a conversation has messages, its mode locks. To search a different source, start a new conversation.

Using Ask

1

Open Ask

Click Ask in the sidebar, or press ⇧⌘O (Mac) / Shift+Ctrl+O (Windows/Linux).
2

Pick a mode

Choose History, Files, or Memories from the pill toggle.
3

Narrow to a bucket (Files and Memories only)

In Files and Memories mode a dropdown lets you scope the search. Leave it on All files or All memories to search everything, or pick one bucket for focused results.
4

Ask a question

Type a plain-language question, or click one of the example chips under Try asking:. Press Enter to send.
5

Read the answer and check the sources

The answer streams in. Every answer cites the chats, memories, or files it drew from. Click a source to open the original.
The composer placeholder changes with the mode: Ask about your chat history…, Ask about your files…, or Ask about your memories…. A Think toggle turns on extended thinking for harder questions, at the cost of a slower answer.

Which mode to pick

  • History when the answer lives in a past conversation: a decision you talked through, advice you got, a thread you half-remember.
  • Files when the answer is in a document you uploaded: a spec, a paper, a contract.
  • Memories when you saved the fact yourself: a preference, a goal, a note.
Ask does not search across modes at once. If you are not sure where something lives, start with the source you last put it in.

Conversations are saved

Ask keeps each conversation in a sidebar and auto-generates a title after your first exchange, so you can return to a line of questioning instead of starting over. If the bucket or file collection behind a saved conversation is later deleted, the conversation becomes read-only: you can still read it, but you cannot send new messages.

How it works

Ask reads your question, retrieves the passages that match it, and writes an answer grounded in those passages.
  • History mode runs semantic search over your conversation archive and synthesizes an answer from the matching segments, with citations back to each chat.
  • Files mode searches the chunks your uploaded documents were split into and answers from the matching passages, including file name and page or section.
  • Memories mode loads context from the selected bucket. For buckets using Smart Memory, it loads category summaries and pulls specific categories as needed. For other buckets, it loads recent memories and searches for anything else the question needs.
Because every answer is grounded in retrieved sources and shows them, the sources are the ground truth. The synthesized answer is a summary; open the originals when the details matter.

Also available outside the dashboard

The same underlying queries are exposed to your AI tools:
  • MCP: the recall_chat_history and search_uploaded_files tools query your chat history and files from any MCP client. See MCP server and Remote MCP server.
  • TypingMind: the plugin’s recall_chat_history and search_uploaded_files functions do the same inside TypingMind. See TypingMind plugin.

Getting better answers

“What did I decide about the API migration timeline?” beats “what do I know about work”. A narrow question retrieves narrower, more relevant sources.
History for past conversations, Files for uploaded documents, Memories for facts you saved. The wrong mode searches the wrong place.
Ask synthesizes; the originals hold the full detail. Click through before you rely on an answer.
Each conversation carries its own context. Unrelated questions in the same thread can pull in stale context.

Requirements

Ask needs a paid plan (Core or Pro, including the trial). Beyond that, each mode needs data to search:
  • History needs imported or synced conversations.
  • Files needs documents in a file bucket.
  • Memories works as soon as you have saved memories.
Chat History imports are plan-limited: Core covers up to 500 conversations from one platform (Claude or ChatGPT), and Pro is unlimited across all supported platforms. This limit shapes what History mode can search.

Next steps

File Buckets

Upload documents so Files mode has something to search

Chat History

Import and sync conversations for History mode