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Introduction to email sync

Connect Gmail or Outlook and see exactly what syncs, what stays private, and what Winston is allowed to do — in plain terms.

Connecting your email is usually the first real setup step in Winston, and it is the one people are rightly most careful about. This article explains what happens when you connect Gmail or Outlook, in plain terms: what gets imported, what Winston can and cannot do with your inbox, and who on your team sees what. Nothing changes in Gmail or Outlook itself — your inbox keeps working exactly as before.

What happens when you connect

When you connect an inbox, three things happen — and this is the complete list:

  • Your past threads import. Winston reads your email history so that existing conversations show up on the right records from day one. A guest who emailed you last year already has their story attached when they email you next.
  • People and company records create themselves. Every sender and recipient becomes a person record, matched to a company by their email domain where one exists. You do not type anyone in — the CRM builds itself from the mail you already have.
  • New mail files itself. From then on, every incoming and outgoing message lands on the matching person's timeline automatically. Reply from Gmail, reply from Outlook, reply from Winston — it all ends up in the same place.

The practical outcome: the next time someone asks "have we talked to this guest before?", the answer is on their record, not in a mailbox search.

What's read — and what's not

Connecting an inbox lets Winston read messages so it can file them to records and keep attributes current — it does not let Winston send anything on its own unless you set that inbox's reply mode to Auto-send.

Winston never sends an email without your approval. When Winston drafts a reply, it stays a draft — clearly marked — until you review it and press send yourself. Only switching an inbox's reply mode to Auto-send changes this.

You stay in control of the connection, too. You can disconnect an inbox at any time from your account settings, and disconnecting stops the sync immediately.

Who on the team sees what

Winston's value comes from shared history, so by default a connected work inbox contributes its threads to the workspace: any teammate who can open a record can read the emails on its timeline. That is what turns five personal inboxes into one front office — the person answering the phone can see the quote a colleague emailed yesterday.

Troubleshooting

If something looks off, two quick checks solve most cases: the initial import of a large mailbox can take a while, so give a fresh connection time to finish; and if a provider password change broke the link, reconnecting the account from settings resumes the sync where it left off.

For anything deeper — send-from-record, calendar sync, signatures, or provider-specific issues — the Email & calendar section of the help center covers email in full detail.

For a video walkthrough, see Email sync, people & company records in Winston Academy.

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