Outlook not connecting

Question

For the past couple of months we have had several users plagued with Outlook not connecting. The user will come in, turn on their laptop and open Outlook. The Outlook icon on the taskbar will have a red exclamation on it and the Outlook Synchronzation Status will show "trying to connect". A simple restart of Outlook does not work. The user must restart their laptop (sometimes twice) for Outlook to finally connect to 365 and send/receive mail.

We are running Office 365 Business in a hybrid environment with Windows 11.

Answer 1

Hi @M. Shane Stecher ,

Welcome to our forum!

What's the version of your Outlook? (File > Office Account > About Outlook). Please make sure you have upgraded your Outlook to the latest version.

And i notice that several users encounter the same issue, do their environments or Outlook clients have anything in common?

As i know, the issue may be related to several factors, please try the following troubleshooting steps:

1.Try to use the Microsoft Support and Recovery Assistant, which works by running tests to figure out what's wrong and offers the best solution for the identified problem.

2.Considering the impact of some add ins, It is suggested that you try to start outlook in safe mode(Win+R>type: outlook /safe) to check whether it works normally.

3.If this is still the issue in safe mode, it is suggested that you could try to create a new profile (Control Panel>Mail>Show Profiles>add) and add the account for testing to check if there are some differences.

4.In addition, i found a thread with a similar issue to yours, it's suggested that you could review and refer to the helpful suggestions mentioned by some users in that thread.

Hope to help you!

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