How to install the new Outlook HubSpot Sales Plugin

If you are one of the countless professionals migrating to the "New Outlook" for desktop, or relying heavily on Outlook for the web, you may have hit a frustrating roadblock: your old HubSpot Sales extension doesn't work the way it used to.

Microsoft’s transition to the "New Outlook" has changed how add-ins operate, moving away from COM-based desktop plugins to web-based add-ins. For sales professionals who live and die by their CRM, this can be a frustrating transition.

In this guide, and accompanying video "How to install the new Outlook HubSpot Sales Plugin (Dec 2025)" we break down exactly how to navigate this change. This guide gives you a detailed walkthrough of the installation process, key features, and best practices to ensure you can use the HubSpot Sales Plugin like a pro.

Why You Need This Plugin (and Why the "New Outlook" Matters)

The core promise of the HubSpot Sales plugin has always been efficiency. As a salesperson, context switching - jumping between your email client and your CRM - is a productivity killer.

The "New Outlook" is here to stay. Microsoft is aggressively pushing users toward this unified experience, which mirrors the Outlook Web Access (OWA) interface.

The "Tab-Switching" Problem

Without the plugin, every time you receive an email from a prospect, you have to:

1. Open HubSpot in a browser.
2. Search for the contact.
3. Check their deal stage.
4. Log your reply manually.
5. Switch back to Outlook to hit send.

With the new HubSpot Sales Office 365 add-in (the specific version required for the New Outlook), this entire workflow happens inside your inbox. You can view CRM data, update deal stages, and enroll contacts in sequences without ever leaving the message pane.

How to install the new HubSpot Outlook Sales Plugin

Step 1: Connect Your Personal Email in HubSpot

Before you even touch Outlook, you must ensure your HubSpot account is ready to communicate with your email provider.

1. Log in to HubSpot.
2. Navigate to Settings (the gear icon in the top right).
3. In the left sidebar, go to General > Email.
4. Click on the Email tab.
5. Look for the option to Connect Personal Email.
6. Follow the prompts to authorize the connection with Microsoft 365.

Step 2: Install the Microsoft-Approved Add-in

Once HubSpot is connected, you need to install the interface in Outlook:

1. Open your New Outlook for desktop or Outlook on the web.
2. Locate the "Get Add-ins" icon (often represented by a square grid or a "store" icon) in the ribbon.
3. In the search bar, type "HubSpot Sales".
4. Look for the HubSpot Sales add-in (ensure it is the "Office 365" version, not the legacy desktop one).
5. Click Add.
6. Once added, open an email, click the HubSpot logo (the sprocket) in the toolbar, and log in with your HubSpot credentials.

Pro Tip: In the New Outlook, add-ins sometimes hide under the "..." (More Actions) menu in an email. Pin the HubSpot add-in to your toolbar so it’s always one click away.

Troubleshooting the "New Outlook" HubSpot Sales Plugin

The shift to the New Outlook has caused confusion because the interface looks different from the classic COM add-in. Here are common issues and fixes mentioned in the broader HubSpot community and alluded to in the video strategy:

"I can't see the sidebar!"

Fix: In the New Outlook, the sidebar doesn't always stay open. You may need to click the HubSpot icon for each email unless you "Pin" the pane. Look for a "Pin" icon in the top right of the HubSpot sidebar to keep it open persistently.

"The 'Log' and 'Track' boxes are missing."

Fix: In the web add-in, these settings are often managed via the sidebar settings rather than checkboxes in the compose window. Ensure your "Log" and "Track" defaults are set up in your main HubSpot settings.

"It says 'Get Add-ins' is blocked."

Fix: This means your IT department has restricted the installation of third-party apps. You will need to request they whitelist the HubSpot Sales extension or deploy it centrally.

Feature Deep Dive: Mastering the Sidebar

Once installed, the sidebar becomes your command center. The video outlines four key areas where this plugin transforms your workflow: Managing Contacts, Sales Activities, Logging, and Deployment.

Managing Contacts: Goodbye Data Entry

The most immediate benefit is the ability to add new leads instantly.

When you open an email from a new prospect, the sidebar will check HubSpot’s database. If the email address isn't found, you’ll see a prompt to "Add to HubSpot."

• One-Click Addition: You don't need to copy-paste names or phone numbers. The plugin scrapes the available metadata from the email header.
• Enrichment: Once added, HubSpot often pulls in company information automatically, populating the contact record with job titles, company size, and industry data.

Sales Activities: Actionable Intelligence

The video emphasizes that the plugin isn't just for viewing data; it's for doing work.

• Create Deals: Did a prospect just reply with a "Yes, let's meet"? You can create a new Deal record right from the sidebar. You can assign the pipeline, deal stage, and amount immediately.
• Tasks & Follow-ups: Instead of writing "Call John next Tuesday" on a sticky note, click the Tasks tab in the sidebar. Set a due date and a reminder. This task will now appear in your daily HubSpot task queue.
• Timeline View: You can scroll through the contact's history to see previous calls, notes, and page views, giving you perfect context before you type your reply.

Logging Emails: The "Association" Game-Changer

Perhaps the most technical but crucial part of the tutorial covers email logging and association.

In sales, you might have multiple deals open with a single company. When a contact replies, which deal does that email belong to?

• Automatic Logging: By default, the plugin logs emails to the contact record.
• Custom Association: In the sidebar, you can verify exactly which Deal or Ticket the email is being logged to. If you are working on a renewal but the client emails you about a support issue, you can uncheck the "Renewal Deal" and check the "Support Ticket" to keep your CRM data clean.
  NOTE: If you have multiple deals for one contact, always check the sidebar before sending crucial contract information to ensure it logs to the correct opportunity.