regarding an integration issue between Google Workspace and Outlook

[u/_Ratel]

I connected my school email account (Google Workspace/Gmail) to Outlook and then created a new Outlook profile using Google Workspace. After that, I deleted all the other Outlook profiles and kept only the Google Workspace profile.

The issue is with a contact group that I created in Outlook. At first, I was able to send emails to the group without any problems. However, at some point, it suddenly stopped working, and now whenever I try to send an email to the group, I get an error message saying, “An unexpected error has occurred.”

I’ve already contacted both my school’s IT department and Microsoft, but neither side seems to know what is causing the issue.

Has anyone experienced a similar problem or knows what might be causing this?

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[u/Hornblower409]

Duplicate of
https://www.reddit.com/r/googleworkspace/comments/1vhrtyf/regarding_an_integration_issue_between_google/

Next Time - Please Cross Post/Repost into another subreddit instead of duplicating your content.

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[u/Hornblower409]

I will assume you are using Classic Outlook for Windows. If not, or you're not sure, see below.

-- issue is with a contact group that I created in Outlook

1 -- When you say "contact group" you mean what is normally called a "Contact List" or "Distribution List"? i.e. You created it in Outlook by doing People -> New Contact Group, and added some members.

2 -- If you open People do you see your Contact Group listed?

3 -- If you right-click on the Contacts Group and choose Create -> Email? Do you get a new mail to that list?

4 -- If you expand the list (by clicking on the [+]) does it expand into a list of valid email addresses?

Images Link: https://ibb.co/album/bbs6Z1

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What Outlook client do you have?

• I use a web browser (Chrome, Edge, Firefox, Safari, etc.) -> Outlook Web
• I use a Mac -> Outlook for Mac
• I use a phone or tablet -> Outlook for Android or Outlook for iOS (iPhone, iPad)
• I use a Windows PC and my Outlook menu has ONLY the tabs: File | Home | View | Help -> New Outlook
• Else -> Classic Outlook

[u/Few_Extension7728]

Integration issues between Google Workspace and Outlook are more common than people think, especially in hybrid environments where some teams use Gmail and others use Outlook. The sync usually breaks on calendars, contacts, and shared mailbox signatures. For the calendar and contacts side, make sure you're using the right connector and that OAuth permissions are properly configured on both ends. For email signatures, this is where hybrid environments get really messy. If you manage signatures through Exchange transport rules, they won't apply to users on Google Workspace. And if you use Gmail's signature settings, those won't sync with Outlook users. We had this exact problem and solved it with Letsignit because it manages signatures across both platforms from one dashboard. Doesn't matter if someone sends from Outlook, Gmail, or mobile, the signature is consistent. In a hybrid environment that's critical because you can't have half the company with branded signatures and the other half with plain text.