AI reply assist and autonomous replies

Draft replies faster with an in-composer AI assistant, let Ken reschedule out-of-office leads automatically, and understand how Ken's autonomous reply agent handles high-intent prospects without waiting on a human.

11 min read · Updated Jun 29, 2026

Overview

Ken ships three distinct AI features that work on replies:

AI reply assist - a human-triggered assistant inside the reply composer that rewrites, shortens, lengthens, or continues your draft on demand.
AI follow-up reminders - automatic detection of timing language in replies ("circle back in Q3") that stamps a follow-up date and resurfaces the reply in your To Reply tab when the time comes.
Autonomous reply agent - a per-campaign opt-in that reads inbound replies, drafts responses, and sends them after a short hold window, with calendar integration for booking requests.

All three features live on the Replies page, accessible from the Replies item in the left sidebar at /replies.

Before you start

You must be a member of an active workspace with at least one campaign running.
To send any reply (assisted or autonomous), at least one inbox must be connected under Deliverability.
The autonomous reply agent is enabled per campaign and requires a connected calendar integration (Calendly, Cal.com, Outlook, or HubSpot Meetings) for booking requests. It is off by default.
AI reply assist requires no setup - it is available to any user who can open a reply thread.

How to draft a reply with AI assist

Step 1 - Open a thread

In the To Reply tab, click any row to open the conversation thread in the side panel.

Step 2 - Open the composer

Click Reply, Reply All, or Forward to open the composer below the thread.

Step 3 - Open the AI assistant

Click the AI button (with the sparkles icon) in the toolbar at the bottom of the composer, or press Ctrl+I from anywhere inside the composer. The AI assistant panel opens below your draft.

Step 4 - Choose an action

The assistant panel shows five quick actions:

| Action | What it does | |--------|-------------| | Rewrite | Rewrites the full draft from scratch while preserving intent. | | Simplify | Removes complexity and jargon. | | Shorten | Makes the draft more concise. | | Lengthen | Expands the draft with more detail. | | Continue | Picks up where the draft ends and adds more. |

You can also type a custom instruction in the Tell Ken what to change field and click Apply.

To run the assistant on a specific passage rather than the whole draft, select that text in the editor first. The panel will show "Working on selected text" to confirm.

Step 5 - Accept or adjust

The generated text appears in the preview area as it streams in. Once done:

Click Accept to insert it into the composer (replacing the full draft or the selection).
Click Regenerate to run the same action again for a different result.
Click Discard (or press Escape) to close the panel without changing your draft.

You can also run a different action while the panel is open to replace the preview.

How to set a follow-up reminder

When a prospect says "let's talk next quarter" or "reach out after the holidays," you can set a reminder so the reply resurfaces automatically.

From the thread panel header

Open the reply thread.
Click the bookmark icon in the thread panel header.
Select Remind me later...
Pick a preset - Tomorrow, Next week, or Next month - or choose a custom date from the calendar.

The reply is bookmarked (visible in the Saved tab) and will reappear in the To Reply tab on the chosen date.

From the row context menu

Right-click any reply row to access the same Remind me later... option without opening the thread.

Marking a reminder done

When you have followed up and no longer need the reminder, open the bookmark dropdown and click Mark reminder done. This clears the reminder but keeps the reply in Saved. It does not archive the reply.

AI-set reminders

Ken reads every inbound reply for timing language. When it detects a future date ("circle back in Q3," "after the holidays"), it silently sets a reminder for you - using the same bookmark control, with no separate notification. An AI-set reminder and a manually-set one look identical. The reply resurfaces in To Reply on the detected date, resolved to the start of the period ("Q3" becomes July 1, "next month" becomes the first of next month).

How the autonomous reply agent works (per-campaign opt-in)

The autonomous agent is a separate, per-campaign feature that is off by default. When enabled, it acts on inbound replies without waiting for a human.

To enable it, go to the campaign's settings and turn on the autonomous reply option. Once on, the agent:

Reads every new inbound reply that the classification system labels as Interested, Objection, Question, or a meeting request. It ignores all other classifications.
Drafts a reply using the same context a human rep would have - the lead's profile, the campaign, and the full conversation thread.
Queues the draft with a hold window (roughly 10 minutes). During this window you can edit or cancel it from the inbox.
Sends automatically if no one acts.

For booking requests, the agent reads real availability from your connected calendar. If no calendar is connected, or if the agent cannot read live availability, it escalates to a human rather than inventing a time slot.

Low-confidence replies are never sent automatically. The agent routes them to a human instead.

How it works

AI reply assist

The composer sends the current draft (or selected text) plus the conversation context to the backend AI service, which streams the response back token-by-token using Server-Sent Events. The result appears in real time in the preview area. The assistant uses the same full context bundle - lead fields, campaign details, and the conversation thread - that the autonomous agent uses, so both surfaces produce the same quality of output.

AI follow-up reminders

Every inbound reply passes through a classification pass. When the classifier detects timing language, it extracts a date and writes it back as a reminder. No extra AI call is made - the extraction rides on the classification pass that already runs for every reply. Fuzzy dates resolve early: "Q3" becomes July 1, "next month" becomes the 1st of next month. This means the reply resurfaces at the front of the window rather than at the end, giving you the most lead time. The date is stored on the reply record; a background query clause checks for due reminders each time you load the To Reply tab.

Out-of-office auto-rescheduling

Out-of-office replies are handled separately from human replies. When an inbound auto-reply is detected, Ken:

Removes the lead from the active campaign immediately, so no further emails go to an empty inbox.
Parses the return date from the auto-reply text.
Schedules a re-enrollment for two days after the return date (or seven days from now if no date was found).
Automatically re-attaches the lead to the campaign on that date.

These replies appear in the Automated tab. No human action is required.

Autonomous reply agent

The agent runs in the background on the reply processing pipeline. It applies a confidence gate before sending: only high-confidence replies queue for auto-send; everything else routes to a human. The hold window gives you a window to override. All autonomous replies are traced and logged, and the feature is gated behind a per-campaign flag that defaults to off.

Troubleshooting & debugging

The AI button is grayed out in the composer.

The composer must be open and the editor must be initialized. If the editor has not loaded yet (e.g. the thread is still loading), the button is disabled. Wait for the thread to finish loading and try again.

The assistant panel opens but nothing generates.

The backend AI assist endpoint timed out or returned an error. The panel displays an error message below the preview area. Check your connection. If the error recurs, reload the page and try again.
A 502 error typically means the upstream AI service did not return a stream. Retry; these are usually transient.

The assistant produces an empty or cut-off result.

The request timed out mid-stream. The maximum allowed duration for a single assist call is 120 seconds. For very long drafts, try using Shorten first and then Continue.

Accepting the AI suggestion does not update the composer.

If the editor lost focus or was unmounted while the assistant was running, the insertion may fail silently. Close and reopen the composer and try again.

A reminder I set is not showing up in To Reply on the right date.

Reminders are surfaced by a query clause that checks reminderDate <= now AND NOT archived. If the reply was archived (moved to Done) before the reminder date, it will not reappear. Unarchive the reply from the Done tab to restore it.
Check that the reply still has a reminder badge in the Saved tab. If the badge is gone, the reminder was already cleared.
Reminder dates are stored in UTC. If you are in a timezone significantly ahead of or behind UTC, the reply may resurface a few hours earlier or later than expected.

An AI-set reminder was set to the wrong date.

The classifier resolves fuzzy dates to the start of the period. "Q3" = July 1, "end of year" = roughly January 1. If this is too early, edit the reminder date by opening the bookmark dropdown, selecting Remind me later..., and picking a new date. The previous date is replaced.

Out-of-office replies are not being rescheduled.

The OOO detection pass fires only on replies the sending provider flags as auto-replies or out-of-office, or on events the classifier itself labels OOO. If a provider sends a non-standard auto-reply without those flags, detection may not fire. Check the Automated tab - if the reply appeared there, the system saw it. If it is not there, the provider did not expose the correct flags and the reply may have landed in To Reply instead.
Re-enrollment runs on a periodic schedule (every 60 minutes). If the reschedule date passed very recently, allow up to one hour for the lead to re-appear in the campaign.

The autonomous agent sent a reply I wanted to edit.

The hold window is the only opportunity to intervene. If the reply sent before you could act, check whether the hold window duration is configured correctly in the campaign settings. You can reply manually to correct the thread.

The autonomous agent is not sending any replies even though it is enabled.

Confirm the campaign status is Active. The agent only acts on live, running campaigns.
Check that the reply classifications are correct. The agent only acts on Interested, Objection, Question, and meeting-request classifications. Replies in Automated, Not Interested, or Done are never touched.
If replies are consistently low-confidence, the agent routes them to a human. This is expected behavior, not a bug.
For booking requests: if no calendar is connected, the agent cannot propose times and will escalate rather than send. Connect a calendar integration to enable autonomous booking.

FAQ

Does AI reply assist send anything automatically? No. The assistant only generates a suggestion. You choose whether to accept, regenerate, or discard it. Nothing is sent until you click the send button in the composer.

Are AI-set reminders different from ones I set manually? They behave identically. The source is recorded internally for measurement but is never shown in the UI. Both show the same reminder badge in the Saved tab.

Can I use AI assist on just part of my reply? Yes. Select the text you want to change in the composer before opening the AI assistant. The panel confirms "Working on selected text" and any action you run applies only to that selection. Accepting inserts the AI text in place of your selection.

What happens if the autonomous agent cannot book a meeting? If no calendar is connected, or if the agent cannot read live availability, it does not guess or invent a time slot. The reply is escalated to the To Reply tab for a human to handle instead.

What reply types does the autonomous agent ignore? The agent never acts on: bounces, unsubscribes, spam complaints, out-of-office replies, other auto-replies, wrong-contact replies, and not-interested replies. Those are handled by separate flows or routed to a human.

Can I turn off the autonomous agent for a single campaign? Yes. The agent is a per-campaign opt-in. Disable it in the campaign settings at any time. In-flight queued replies in the hold window at the moment of disable are still sent (the window has already started); future replies will not be touched.