Generate vs Rewrite in Gmail: Which Context Is Used?

Side-by-side: Gmail Generate Reply can use thread, reply prompt, knowledge base, and What I want to say. Rewrite Message uses rewrite prompt and draft only. When to pick each.

Gmail and Email OutreachPublished Reading time 5 min

You are in Gmail compose and AGNURA shows two AI actions: Generate Reply and Rewrite Message. They look similar. They send different context to managed AI.

Best for summary

Your situationPrefer
You need a reply grounded in the conversationGenerate Reply
You already have wording and want a polish passRewrite Message
You want the model to use your knowledge baseGenerate Reply
You want to avoid sending thread history againRewrite Message

This page compares the two approaches inside AGNURA AI Assistant (made by AGNURA). It is not a vendor bake-off against another product. For the step-by-step Generate Reply path, see How to Generate a Gmail Reply With Thread Context. Hub: Research-to-Email Outreach: From Website Context to a Reviewed Gmail Draft.

Direct answer

Generate Reply can send your reply prompt, optional What I want to say, shared knowledge base, and the Original email / thread text.

Rewrite Message sends your shared rewrite prompt and the compose draft only. It does not load thread history or knowledge base by design.

Neither action sends mail. You review, insert, and click Send in Gmail.

Comparison criteria

CriterionWhat we mean
Primary jobNew reply vs polish existing draft
Context sent to managed AIWhich fields leave the browser on click
Prompt sourceEmail reply prompt vs shared rewrite prompt
Thread / conversationLoaded or not
Knowledge baseIncluded or not
One-run steeringWhat I want to say available or not
Insert behaviorManual insert; quoted thread handling
Privacy surfaceHow much conversation text is transmitted
FitWhen each action is the better first click

Side-by-side: what each action is strong at

Generate Reply

Strengths

  • Builds a reply when the compose box is empty or thin
  • Can expand/scrape the Gmail thread (best-effort Expand all, then scrape)
  • Uses standing Reply prompt (Settings → Email Prompts)
  • Can include shared knowledge base for facts about you/your offer
  • Optional What I want to say steers this one run without saving to Settings
  • Steers the model to write as you; follow-up vs reply depends on who spoke last in the loaded thread

Trade-offs

  • Sends more context (thread + KB) to AGNURA managed AI (credits)
  • Thread load can fail or truncate; you may need Edit + paste
  • Not the right tool if you only want to rephrase a finished paragraph

Rewrite Message

Strengths

  • Fast polish of text already in compose
  • Smaller context bundle: rewrite prompt + draft only
  • Shared Rewrite Prompt (same settings store used across Gmail, LinkedIn, WhatsApp, Reddit rewrite actions)
  • Insert into message replaces your draft while keeping quoted thread content below
  • Better when you do not want to re-transmit the full conversation

Trade-offs

  • Will not “catch up” on messages missing from the draft
  • Does not use knowledge base or thread scrape
  • Weak if the compose box is empty

Context map (what managed AI receives)

InputGenerate ReplyRewrite Message
AGNURA sign-in + modelYesYes
Reply prompt (replyPrompt)YesNo
Rewrite prompt (rewritePrompt)NoYes
What I want to sayYes (optional)No (rewrite modal is draft/prompt focused)
Knowledge baseYes (or none)No
Original email / threadYes (auto-load or paste)No
Compose draft as sourceNot the primary sourceYes (loaded from compose)

Both calls are user-triggered. Nothing is sent until you click Generate Reply or Rewrite in the modal.

Decision framework

If…Then…Because…
The reply box is empty and you need an answer to their last emailGenerate ReplyThread context is the main input
You already wrote most of the reply and want clearer wordingRewrite MessageDraft-only context matches the job
You need a fact from your knowledge base in the answerGenerate ReplyKB is included there
The thread is sensitive and you already summarized the point in draftRewrite MessageSmaller payload
You sent the last message and need a nudge follow-upGenerate Reply (with thread loaded)Product steers follow-up vs reply from last speaker
You only need linkify or dictationUse Convert links or Voice to TextThose are different menu actions

You can combine them: Generate Reply → edit → Rewrite Message for a final polish. Still review before Send.

Pricing and usage notes

ItemNote
AGNURA extensionFree Chrome install
OpenAI usageUses AGNURA credits for both Generate and Rewrite
Local settingsPrompts, KB, Activate Gmail stored in chrome.storage.local
Last verified2026-10-02 (product behavior from current AGNURA Gmail compose docs/source)

Local settings are not the same as local AI inference. Generate/Rewrite calls managed AI. See Local Settings vs Local AI: The Privacy Difference.

Poor-fit cases

ActionPoor fit when…
Generate ReplyYou only want to rephrase a finished draft; you refuse to send thread text to managed AI; thread will not load and you will not paste
Rewrite MessageCompose is empty; you need the model to read the full prior email; you expect knowledge-base facts to appear automatically
EitherYou want auto-send, inbox search across all mail, or Gmail API automation. AGNURA does not do those jobs

How this fits the AGNURA Gmail workflow

Both actions live under the AGNURA AI compose menu when Activate Gmail is on:

  1. Convert URL and email to links
  2. Generate Reply
  3. Rewrite Message
  4. Voice to Text

Generate Reply owns conversation-aware drafting. Rewrite Message owns draft-only rewriting. First-touch outreach from a website still starts in the popup (Send Email / Generate AI Email), not these two buttons: How to Personalize an Outreach Email From Website Research.

Related guides

Soft next step

Open one real Gmail reply. If the box is empty, run Generate Reply once. If you already have a draft, run Rewrite Message once. Compare the context fields in each modal before you insert. Install AGNURA if you need the menu:

Add to Chrome

Try AGNURA in Chrome

Draft in Gmail, LinkedIn, WhatsApp, and Reddit. You review every message before send.

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