HubSpot Sales prompts login every time Outlook on desktop is opened

If you've found that you need to log into HubSpot Sales every time you open Outlook on Windows desktop, or when logging into the HubSpot Sales for Windows tray app, you'll need to make some changes to your configuration in Internet Explorer. 

Please note: these steps apply to the HubSpot Sales Outlook desktop add-in. If you have the HubSpot Sales Office 365 add-in, follow the troubleshooting steps for that add-in instead.

• Open the Control panel on your Windows device, then use the search bar to look up and select Internet Options. 

• In the Internet Options dialog box, click the Security tab.
• Select the Trusted Sites icon.

• Click the Sites button.

• Add each of the following URLs to the Add this website to the zone field, one at a time. Click Add after entering each one:
  • https://dl.getsidekick.com
  • https://app.getsidekick.com
  • https://app.hubspot.com
• Once you've added all three URLs, click Close.

• In the Security level for this zone section, set the security setting to Low.

• Next, click on the Privacy tab and click Advanced.

• Select the Accept radio button for both First-party and Third-party cookies (if the options are grayed out, select the Override automatic cookie handling checkbox).
• Select the Always allow session cookies checkbox.
• Click OK.

• Click Apply.
• Try logging into the Outlook desktop add-in or Windows tray app again.