topic HubSpot Sales Add-in keeps disconnecting in Outlook for Mac — real risk for email tracking reliabili in Outlook Sales Extension

HubSpot Sales Add-in keeps disconnecting in Outlook for Mac — real risk for email tracking reliabili

CMancel — Tue, 22 Jul 2025 07:41:40 GMT

We’re experiencing a recurring issue with the HubSpot Sales add-in for Outlook on Mac: the add-in keeps disconnecting, forcing users to reconnect regularly. In practice, this means that most team members simply stop using the add-in — or don’t even realize they’ve been disconnected — and as a result, emails are no longer properly tracked in HubSpot.

This has a direct impact on our sales and client follow-up processes:

Critical conversations aren’t logged
No visibility on who opened or engaged with emails
Incomplete reporting and pipeline visibility

The “workaround” would be to force everyone to use Outlook web instead of the native app, but let’s be honest — that’s not realistic for most teams. The Outlook web experience simply isn’t as good or as integrated as the desktop app, and you can’t expect every user to change their habits just to keep HubSpot working.

This is a serious limitation. If the add-in can’t stay connected reliably on the main platforms people use, HubSpot tracking becomes optional and easily forgotten, undermining the whole point of integrated sales tracking.

If anyone has found a sustainable fix or workaround for Mac (other than “just use the web version”), I’m interested. Otherwise, I’d really like to see HubSpot address this gap for Mac desktop users — reliable, seamless tracking needs to be the baseline, not the exception.

Let me know if you want it tailored for a specific audience (internal, LinkedIn, HubSpot Community, etc.).

Re: HubSpot Sales Add-in keeps disconnecting in Outlook for Mac — real risk for email tracking re...

Jaycee_Lewis — Tue, 22 Jul 2025 17:17:57 GMT

Hey, @CMancel, thanks for the feedback. This is a great fit for our Ideas Forum. — Jaycee

Re: HubSpot Sales Add-in keeps disconnecting in Outlook for Mac — real risk for email tracking relia

MichaelSa — Tue, 07 Oct 2025 15:19:22 GMT

I'm also having this issue. Further, after logging in repeatedly, the tracking BCC isn't added to emails automatically, so if/when a contact replies, the "rest" of that conversation is lost.

Re: HubSpot Sales Add-in keeps disconnecting in Outlook for Mac — real risk for email tracking relia

STierney — Tue, 07 Oct 2025 15:55:38 GMT

Hey @MichaelSa - thanks for posting in the Community!

I understand that you're having two issues here:

1. Your Outlook Sales Extension keeps disconnecting
2. The tracking BCC isn't being added to your emails automatically

I'd like to first clarify that as noted here, you've activated the newer, HubSpot Sales web add-in, linked above. You'll see that due to the significant changes introduced by Microsoft as part of the new Outlook for Windows, HubSpot will no longer actively develop or improve the HubSpot Sales Outlook desktop add-in. While the HubSpot Sales Outlook desktop add-in is still available in the old Outlook for Windows and will continue to be supported, it's highly recommended that you activate the HubSpot Sales web add-in instead. If you're using the Outlook desktop add-in, the HubSpot Sales web add-in will automatically be installed if you switch to the new Outlook for Windows. You can learn more in this HubSpot Community post.

Additionally, regarding the BCC, it's noted here that while we expect emails to automatically log with the Sales extension, you would need to manually add the BCC address to see your emails logged. The steps for this can be found here.

Shane, Senior Community Moderator

Re: HubSpot Sales Add-in keeps disconnecting in Outlook for Mac — real risk for email tracking relia

MichaelSa — Tue, 07 Oct 2025 16:08:13 GMT

This is really unfortunate. The “new” outlook is cr@p. The

I know that HS doesn’t care about a single user’s attrition, I upgraded my subscription yesterday in the hopes that a bigger spend would deliver better functionality, but alas, that appears to not be the case.

Yes, I’m on the latest version of the plugin.