Quick answerSend a proactive digest on a fixed quarterly cadence to customers who never asked for one, separate from your changelog and separate from any incident-driven disclosure. Quarterly is frequent enough to catch meaningful drift in a fast-moving agent and infrequent enough that customers actually read it instead of tuning it out. Keep it short: three to five behavior or capability changes that would plausibly affect how the customer uses the agent, written for someone who has not been following your release notes.
This is a push decision, not a documentation decision
There is already a place for a full record of what changed, a changelog customers can actually read if they go looking for one. The question this post answers is different: should you proactively push a summary to customers who never went looking, and if so how often and in what format. A changelog is pull. This is push.
Most companies get this wrong in one of two directions. Either they never push anything and rely entirely on customers checking the changelog, which almost none of them do, or they push every individual change as it ships, which trains customers to ignore the notifications entirely within a few weeks.
Why quarterly is the right default cadence
Monthly is usually too frequent for behavior and feature changes specifically, even though it might be right for a security bulletin. Most individual changes are not significant enough on their own to justify interrupting a customer's inbox, and bundling too small a set of changes into each update makes the update feel like noise. Annual is usually too infrequent, an agent that has meaningfully changed how it handles a category of request over twelve months without a heads-up will produce a wave of "why is it doing that now" support tickets when the drift finally becomes noticeable.
Quarterly threads that needle: enough material accumulates to make each update feel substantive, but not so much time passes that customers are surprised by drift they should have been told about sooner.
What belongs in the proactive digest versus what does not
Include: any change to how the agent makes a decision that customers might have built a workflow or expectation around, any new capability that solves a problem customers have been asking about, and any deprecation of a behavior customers may be relying on. Exclude: internal model version bumps with no customer-visible behavior change, minor prompt tuning, and anything already covered by an incident-specific disclosure.
That last exclusion matters. If your agent made a specific, isolated mistake, that gets its own proactive disclosure at the time it happens, it does not wait for the next quarterly digest. And if what you are measuring is aggregate accuracy over time rather than a list of behavior and feature changes, that belongs in a recurring transparency and accuracy report, a different document with a different purpose, numbers rather than a changelog-style narrative.
Format: short, narrative, and specific to the customer's plan
Do not send the full engineering changelog as the customer digest. Write three to five items in plain language, each one framed as "this means you can now..." or "this means the agent will now..." rather than as a technical description of the underlying change. Segment by plan or feature usage if you can, a customer who never uses the phone channel does not need to read about a voice-handling improvement.
FAQ
What if nothing meaningful changed in a given quarter? Skip that quarter's digest rather than padding it with minor items to hit the cadence. A digest that is sometimes empty and gets sent anyway trains customers to stop opening it.
Should this go to every customer or only active ones? Only customers with activity in the reporting period. A dormant account does not need a behavior-change update for behavior it is not currently experiencing.
Does an urgent, customer-impacting behavior change wait for the next quarterly digest? No. Anything urgent enough to change how a customer should be using the agent right now gets its own immediate communication. The quarterly digest is for cumulative, non-urgent drift, not a substitute for timely disclosure.