How to Set Up the Outlook Extension for HubSpot (And Avoid the Common Pitfalls)

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If you’re using HubSpot and Outlook together and scratching your head about how the extension works (or why it isn’t working the way you think it should), you’re not alone. This is one of the most common topics we cover with our clients, so we decided to break it all down in a straightforward, no-BS guide.

Let’s walk through everything you need to know about setting up and using the HubSpot Outlook extension—whether you're on a Mac or PC, using the desktop app or the browser version.

Step 1: Use the Right Outlook Version for HubSpot

Before you even think about clicking “install,” you need to know this:

✅ Use Microsoft 365 (Office 365) with Outlook

HubSpot no longer supports the old desktop Outlook add-in, so you’ll want to make sure you’re using the Microsoft 365 version of Outlook. This is the one that works directly with the HubSpot Sales Office 365 add-in.

⚠️ Mac Users: Pay Attention

If you're on a Mac, make sure you're using the Outlook app that comes through your Microsoft 365 subscription—not the standalone version that you downloaded individually. That version won’t work properly with the HubSpot extension.

✅ Windows Users

You’re probably already set up correctly if you’re using Microsoft 365. Most organizations using Outlook on PC have already been funneled into the proper setup automatically.

Step 2: Remove the Old Add-In (If You Have It)

If you still have the old HubSpot desktop extension installed, remove it. You can’t have both the legacy extension and the new Office 365 add-in running at the same time—it’ll cause conflicts and headaches.

Step 3: Connect Your Inbox + Enable Automation

Once the extension is installed, connect your inbox and enable inbox automation. There’s a checkbox during setup called:

Automatically log emails to HubSpot

Turn that on.

When it’s enabled, your emails will log to HubSpot automatically when you’re communicating with contacts. This helps cut down on all the manual work and ensures nothing slips through the cracks.

Step 4: Verify the Outlook Extension Is Working

After installation, go to your Outlook inbox and open an email. You should see the HubSpot Sales extension appear at the top when you’re replying or reading a message.

Pro tip: The extension only activates when you’ve actually clicked into an email, so if it looks grayed out—just click into the message and it should appear.

Step 5: Configure Your HubSpot Log and Track Settings

Click into the extension settings. You’re looking for the section labeled:

Log and Track Settings

Make sure the following are enabled:

• ✅ Log Email
• ✅ Track Email

Then, check your default associations. We usually recommend selecting:

• Existing Contacts
• New Contacts
• Companies
• Deals

You can also include Tickets if that’s part of your workflow, or turn off any you don’t want HubSpot to auto-associate.

Bonus Tip: What to Expect When Sending Emails

When replying to someone (even if it’s a junk email from a fake "Lisa"), you'll see that the log and track boxes are checked by default if you’ve configured things correctly. You can always adjust or uncheck them per email, or select specific associations depending on the situation.

Why This Matters

If you're managing sales or client communication through Outlook and you're not syncing it properly to HubSpot, you’re likely:

• Missing important contact records
• Failing to track key conversations
• Spending too much time manually logging emails

Setting this up the right way reduces your administrative workload and ensures your team is always working with up-to-date data in HubSpot.

Final Thoughts + Next Steps

This setup is just the tip of the iceberg when it comes to using HubSpot effectively. While this is one of the first things we set up for our clients, there’s so much more you can do once the basics are in place—like automating sequences, creating smart workflows, and scaling outreach.

If you’re struggling with HubSpot setup or want to take things to the next level, book a call with our team—link’s in the description below. Let’s get your tools working for you, not the other way around.

TL;DR: Outlook + HubSpot Setup Checklist

✅ Use Microsoft 365 version of Outlook
✅ Remove the legacy desktop add-in
✅ Enable inbox automation
✅ Set log and track settings
✅ Double-check your associations
✅ Start emailing and let HubSpot do the work

Need help? We’re here for that. Let’s chat!

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