Outlook Emails Not Logging in HubSpot? Here’s How to Fix It (2026 Guide)

There’s nothing more frustrating than realizing a week’s worth of client emails never made it into HubSpot.

You’ve been following up, answering questions, moving deals forward, and then you open the CRM, and none of it is there. No activity. No record. No visibility.

When the HubSpot Outlook integration isn’t logging emails correctly, the inconvenience becomes secondary to the blind spots it creates. Reporting gets messy, coaching gets harder, and your CRM stops being the source of truth it’s supposed to be.

The good news? Most Outlook logging issues aren’t complex technical failures. They’re usually small settings like a disconnected inbox, a flipped toggle, an unpinned sidebar, or a missing mobile workaround. Let’s walk through how to fix it.

Step 1: Make Sure Your Outlook Inbox Is Actually Connected to HubSpot

Before you troubleshoot anything else, start here.

If your inbox isn’t properly connected, no amount of toggling inside Outlook will fix the issue. HubSpot must be actively connected to your Microsoft account to log and track emails.

Here’s how to check:

1. In HubSpot, click the Settings gear in the top navigation (You can also go to Profile & Preferences — both lead to the same place.)
2. Navigate to General → Email
3. Look for your inbox in the table

You want to see your email address listed, inbox type (e.g., Outlook 365), and status showing ‘Enabled.’

If you don’t see your inbox listed:

• Click Connect inbox
• Follow the Microsoft authentication prompts
• Accept the permissions
• Turn Inbox Automation ON when prompted

Don’t miss that last toggle. If inbox automation is off, emails won’t log automatically, even if everything else looks connected. This is a common reason for 'silent' logging failures—make sure it’s toggled ON before you leave this screen.

If Your Inbox Shows “Not Enabled”

Sometimes connections break. It happens after password changes, security updates, or Microsoft permission resets. If your status isn’t enabled.

• Click Actions
   
• Select Remove
   
• Reconnect the inbox from scratch

It only takes a minute, and it resolves a surprising number of logging issues.

Step 2: Install & Configure the HubSpot Outlook Add-In

Connecting your inbox inside HubSpot is only half the setup. To log and track emails directly from Outlook, you also need the HubSpot Sales add-in installed inside Outlook itself.

Here’s how to install it manually:

1. Open the Outlook desktop app
2. Click the three dots in the top toolbar 
3. Select Get Add-ins
4. Search for HubSpot
5. Choose HubSpot Sales
6. Click Add

• Open an email or start composing a new one
• Look for HubSpot Sales in the top ribbon
• If it’s not visible there, click Apps — it may be nested in that dropdown

When the sidebar opens, you’ll see contact details for anyone already in your CRM. If the email address isn’t in HubSpot yet, you’ll have the option to Add to HubSpot directly from Outlook.

But don’t stop there.

Open Add-In Settings First

Before you start sending emails, scroll to the bottom of the HubSpot sidebar and click:

Add-in Settings → Log and Track Settings

This is where most logging problems start, and where they’re usually fixed.

In the next section, we’ll break down the exact toggles that determine whether your emails log correctly.

The 4 Settings That Control Whether Emails Log in HubSpot

Inside the Outlook add-in settings, there are four key toggles that determine what happens to your emails. If emails aren’t logging, one of these is usually the reason.

Let’s break them down.

1. Log Email

This controls whether a copy of your email is saved to HubSpot. When Log Email is enabled:

• A copy of the email is stored on the contact’s timeline
• It appears under the Email activity type
• The full thread (to/from, timestamps, etc.) is preserved

If this box is unchecked, HubSpot won’t store the conversation, even if your inbox is connected. If your emails aren’t showing up in the CRM, check this first.

2. Track Email

Tracking is different from logging. When Track Email is enabled:

• You can see if the recipient opened the email
• You can see if they clicked links
• HubSpot records engagement behavior

Tracking does not save the email itself; it only monitors activity. Most sales teams want both Log and Track enabled.

3. Create New Contacts

This setting determines what happens when you email someone who isn’t already in your CRM. 

If enabled:

• HubSpot can create a new contact automatically
• Future emails will log properly to that record

If disabled:

• Emails to unknown contacts won’t create a record
• You may need to manually add them later
• Past emails may need to be re-logged

Before turning this on or off, check with your system admin. Some companies prefer tighter control over new records entering the database. But if you’re actively prospecting, this setting can save you from losing conversations.

4. The “Never Log” List

This is one of the most overlooked settings and one of the most common causes of confusion. The Never Log list blocks emails from certain domains or addresses from being logged automatically.

For example, many teams add:

• Their internal company domain
• Shared inboxes
• Vendor domains

If an email address is on the Never Log list:

• The logging checkbox may be disabled
• Emails won’t log automatically

You can still manually choose other records to log to (like a company, deal, or ticket), but contact logging will be restricted.

If logging suddenly stops for specific emails, check this list. Once these four settings are configured correctly, most logging issues disappear.

But if you’re managing a team, there’s one more layer that can override everything, and that’s admin-level defaults.

For Admins: How to Set Default Logging for Your Entire Team

Even if individual users configure their Outlook add-in correctly, settings don’t always stay that way. Extensions might update, preferences can be toggled off, new team members join without proper setup, and suddenly, emails stop logging again.

If you’re a HubSpot admin, you can reduce this risk by setting default logging and tracking behavior at the account level:

1. Go to Settings 
2. Navigate to Data Management → Objects → Activities
3. Select Email
4. Find the Log and Track settings

From there, you can make logging and tracking the default for all users with connected inboxes, and even override individual preferences for the Sales extension.

When these defaults are enabled, emails log automatically unless someone intentionally turns it off. That means fewer gaps in activity, cleaner reporting, and less time troubleshooting “missing” emails.

Why the HubSpot Sidebar Keeps Disappearing (And the One-Click Fix)

You open Outlook, and the HubSpot Sales sidebar is there. Click into another email, and it’s gone. Start drafting a message… still gone.

This is one of the most common usability frustrations with the HubSpot Outlook integration, and it’s not a bug. It’s just a setting.

By default, the HubSpot sidebar doesn’t stay visible as you move between emails or tabs in Outlook. The fix is simple: At the top of the HubSpot Sales sidebar, click the pin icon.

When the sidebar is pinned, it stays open as you:

• Switch between emails
• Draft new messages
• Navigate different folders

If it’s not pinned, Outlook treats it like a temporary window and closes it as you move around.

One more thing to watch for:

If you double-click an email and open it in a new window (common in the desktop app), the sidebar may not stay pinned in that new window. If it disappears, just reopen the HubSpot Sales add-in and pin it again.

It’s a small habit, but it prevents a lot of “why isn’t this logging?” confusion.

Still Not Logging? Run Through This Quick Checklist

If emails still aren’t showing up in HubSpot, don’t panic. Most issues come down to one of a few small settings.

Run through this checklist:

• Is your inbox connected and showing “Enabled”?
  If not, remove and reconnect it.
• Is Inbox Automation turned on?
  Without it, emails won’t log automatically.
• Are both “Log” and “Track” enabled in the add-in settings?
  Logging saves the email. Tracking monitors engagement. You usually want both.
• Is the contact on your “Never Log” list?
  If the domain is blocked, logging may be restricted.
• Is the HubSpot sidebar pinned?
  If it disappears when switching tabs, logging can become inconsistent.
• Are you sending from mobile without the BCC address?
  Mobile emails won’t log unless you manually include your HubSpot BCC.
• Are admin-level defaults overriding user settings?
  In some accounts, logging behavior is controlled centrally

In most cases, one of these fixes resolves the issue within minutes.

Make Sure Your CRM Tells the Full Story

Your CRM is only as good as the activity inside it. If emails aren’t logging consistently, you’re missing context. Managers can’t see real engagement, reports become unreliable, and conversations that move deals forward disappear.

Fixing your connection today is a great start, but keeping your CRM accurate requires staying ahead of the next update or setting change.

If you want more practical HubSpot tips like this, join our HubSpot Hacks newsletter. We share the same strategies and quick fixes we use with our own clients, so your system works the way it should.