Winston

Privacy Policy

Effective date: 22 August 2026

Winston is a personal executive assistant that runs as an app on your Mac. This page explains what data Winston touches, where it lives, what leaves your computer, and what we keep. We have tried to write it the way we would want it explained to us: plainly, and without promises we cannot keep.

What Winston is

Winston is a Mac desktop app. It reads your email, calendar, and the document folders you choose, finds the obligations and deadlines inside them, and helps you plan your time. Your working data lives in a database on your Mac, not in our cloud.

What Winston accesses

When you connect your Google account, Winston asks for these permissions:

• Gmail, read only. Winston reads your mail to find commitments, deadlines, and things waiting on you. He does not send email, and he cannot. When Winston helps you write a reply, the draft is created and shown inside Winston; you copy it into your own mail client and send it yourself.
• Google Calendar, read and write. Winston reads your calendar to understand your time, and creates or moves his own planning blocks. He can only change events he created or events you explicitly ask him to change, and every change is shown to you and can be undone.
• Google Drive, narrow access. Winston uses the narrowest Drive permission Google offers (drive.file). He can create working documents and open files he himself created. He cannot see, list, or read the rest of your Drive.
• Local folders you choose. If you point Winston at folders on your Mac (his Library), he reads and indexes the documents in them so he can find obligations and answer questions about them. You choose the folders; nothing is scanned that you did not choose.

You can disconnect Google at any time from Winston's settings. Disconnecting revokes Winston's tokens with Google and deletes them from your Mac.

Where your data lives

Your mail, calendar cache, documents, commitments, chat history, briefs, and activity log are stored in a local database on your Mac. Backups, when you make them, are local files encrypted with a passphrase you choose. We do not have a copy of this database and cannot read it.

What is transmitted, and to whom

Winston uses an AI model to understand your mail and documents. To do that, relevant content (for example, the body of an email being analyzed, a document passage, or your chat message) is sent over an encrypted connection to our gateway server, which forwards it to our model provider (Anthropic) for processing. This means some of your content does leave your Mac while it is being processed. We will not tell you otherwise.

What happens to that content:

• Our gateway forwards it and does not store it. No request or response content is retained on our servers. Server logs record status codes and field names, never content.
• For each model call, our server keeps one usage record: the operation name, the model used, token counts, timing, and whether the call succeeded. These records contain no message content.
• The results Winston accepts (for example, a commitment title or a quoted excerpt that backs it) are stored back in the local database on your Mac, like everything else he knows.

What we store on our servers

Our servers (hosted on Supabase) store your account, not your life:

• Your email address and authentication identity, used to sign you in.
• Your display name and timezone.
• A record of the device you signed in from, which currently includes your computer's name as set in macOS. Many people's computer names include their own name; you can change your computer's name in macOS System Settings if you prefer.
• The usage records described above.
• Operational receipts, described in their own section below.
• Anything you write in "tell the builders", if you choose to write something. Those are your own words, sent deliberately, and we keep them so we can act on them. They are not covered by the 30-day deletion below, because deleting a message you sent us on a timer would discard the message rather than protect you. Ask us and we will delete it.

The receipts Winston sends

This section exists because the previous version of this page said Winston had no analytics and did not phone home. That stopped being true, and saying so plainly is the point of writing it down.

There are two kinds, and they are deliberately kept separate.

Operational receipts, which are always sent. So that we can help when something goes wrong without asking for access to your computer, Winston reports:

• which version of Winston you are running, and on what kind of Mac,
• that an account was created, and that this device registered to it,
• which steps of setup you reached, and where you stopped,
• when a connection changes state, and the reason code when one fails,
• when a sign-in attempt fails, and why.

These carry codes, counts and timestamps only. No message, no subject line, no email address, no name, no calendar event, no file, no file path. That is enforced in the code itself: anything that is not a short machine-readable code is replaced with the word unclassified before it can be sent, and a test tries to sneak personal text through and fails if any of it survives.

They are linked to your account. We are saying that plainly rather than calling them anonymous, because they are tied to the device record described above and calling them anonymous would be untrue.

We do not offer a switch for these, and we would rather explain why than pretend it is a choice: without them, "Winston isn't working" is something we cannot investigate at all for the people most likely to say it.

Usage receipts, which are off unless you turn them on. If you opt in under Settings, Winston also reports which screens you open and whether you approve or decline what he proposes. Counts only, never content. Winston behaves exactly the same whether this is on or off, and you can turn it off again at any time.

Both kinds are deleted after 30 days, by a job that runs every night.

What Winston does not do

• Winston does not send email. Ever. Drafts are written inside Winston and you send them yourself, from your own mail client.
• Winston does not track what you do inside other apps, does not read your screen, and has no advertising or third-party analytics of any kind. The only things Winston sends are: sign-in, the device record, the AI gateway calls described above, the receipts described above, and anything you deliberately write to us.
• Winston never sends the CONTENT of your mail, calendar or files anywhere except as part of an AI gateway call you triggered, and never to anyone else at all.
• We do not sell your data, share it with advertisers, or use it to train models.

How long data is kept

• Data on your Mac stays until you delete it. There is currently no automatic cleanup or expiry of local data, including old mail content Winston has cached. Deleting it is in your hands, and we explain how below.
• Server usage records and your account record are kept while your account exists.
• Receipts, both kinds, are deleted after 30 days. This is done by a scheduled job rather than being a statement of intent.
• Anything you wrote to us in "tell the builders" is kept until you ask us to delete it, because it is a message you chose to send.

What you can do today

• Disconnect Google. In Winston's settings. This revokes Winston's access tokens with Google and deletes them from your Mac. You can also revoke Winston's access yourself at any time at myaccount.google.com/permissions.
• Delete your local data. Quit Winston, delete the app, and remove the folder at ~/Library/Application Support/Winston. That folder holds the database and everything in it. There is not yet a single in-app button that does this; we say so because promising one would be untrue.
• Ask us to delete your account. Email us at support@winstonsystems.ai and we will delete your server-side account record and usage records.

Google API Services: Limited Use disclosure

Winston's use and transfer of information received from Google APIs adheres to the Google API Services User Data Policy, including the Limited Use requirements.

Specifically: Winston only uses Google user data to provide the features described on this page. We do not transfer Google user data to third parties except as necessary to provide those features (processing by our model provider, as described above), to comply with applicable law, or as part of a merger or acquisition with notice to you. We do not use Google user data for advertising. We do not allow humans to read your Google user data unless you have given us explicit permission for specific data, it is necessary for security purposes, it is required to comply with law, or it has been aggregated and anonymized. Google user data is not used to train generalized artificial intelligence or machine learning models.

Children

Winston is not directed at children under 13, and you must be old enough to hold a Google account in your country to use it.

Changes to this policy

If we change this policy, we will update this page and the effective date at the top. If a change is significant (for example, if we ever add crash reporting), we will say so in the app before it takes effect.

Contact

Questions, requests, or concerns: support@winstonsystems.ai.