Symptom: The HubSpot panel inside Outlook (the sidebar where you log emails, track opens, and start sequences) keeps signing out and asking you to log into HubSpot again, often every time Outlook is reopened.
Important: This is the HubSpot Sales add-in losing its session, not Outlook
or your Microsoft account signing you out. (If Outlook/Microsoft itself logs you out,
that's a different problem, see 00_START_HERE_Email_Summary.md, Part 4.)
Source: HubSpot Knowledge Base + Community, verified June 2026.
Do this first (fixes it for most people)
Sign into the HubSpot add-in with email + password, NOT "Sign in with Microsoft/Google."
HubSpot states it plainly: "If you're using a third-party login method like Microsoft, the cookie will be lost after closing Outlook, and you'll have to log in again."
Steps: 1. In the HubSpot add-in panel, sign out. 2. Sign back in by typing your HubSpot email + password. 3. Check "Remember me." 4. Do not click the "Sign in with Microsoft" / "Sign in with Google" button.
That single change stops the every-reopen logout for most users.
If it still logs out, work down this list
2. Allow third-party cookies
The add-in runs in a webview that requires third-party cookies. If they're blocked,
the session can't persist.
- In the browser the add-in uses (Edge/Chrome) → cookie settings → allow third-party
cookies, or whitelist [*.]hubspot.com.
- On Mac/Safari: Safari → Settings → Privacy → uncheck "Prevent cross-site tracking."
3. Increase the inactive-session timeout (Super Admin)
A short timeout logs you out after idle time (e.g., 24h). - HubSpot → Settings → Account Defaults / Security → Inactive session timeout → set a longer duration. (Requires Super Admin.)
4. Make sure you're on the Office 365 add-in (not the old desktop one)
HubSpot no longer develops the Outlook desktop add-in (due to "New Outlook" changes), it's the version notorious for "prompts login every time." - Remove the legacy desktop add-in and install/activate the HubSpot Sales Office 365 add-in (the supported, web-based one).
5. Clear the slate
- Clear the add-in/browser cache, restart, sign in again.
- Windows Credential Manager → Windows Credentials → remove stale HubSpot / email entries.
- Confirm security software / network filtering isn't blocking the add-in or
*.hubspot.com.
Mitigation: you may not need the add-in for basic logging
If outgoing-email logging is set up as a server-side Auto-BCC rule (see
CEO_Outlook_Stack.md, Section 3), your sent mail logs to HubSpot even when the
add-in is signed out, it runs on the mail server, not the add-in. Then the add-in
login only matters for the advanced features (open/click tracking, sequences), which
the fixes above are meant to stabilize.
Sources
- HubSpot KB, HubSpot Sales prompts login every time Outlook is opened: https://knowledge.hubspot.com/connected-email/hubspot-sales-prompts-login-every-time-outlook-on-desktop-is-opened
- HubSpot KB, Troubleshoot the HubSpot Sales Office 365 add-in: https://knowledge.hubspot.com/connected-email/troubleshooting-the-hubspot-sales-office-365-add-in
- HubSpot KB, Troubleshoot the HubSpot Sales Outlook desktop add-in: https://knowledge.hubspot.com/connected-email/troubleshoot-the-hubspot-sales-outlook-desktop-add-in
- HubSpot Community, Outlook Add-On Keeps Signing Out: https://community.hubspot.com/t5/Outlook-Sales-Extension/Outlook-Add-On-Keeps-Signing-Out/m-p/937423