Desktop Outlook M365 intermittently gives "Trying to Connect" error

Jeff Richard 6 Reputation points
2022-11-10T16:27:30.843+00:00

Having issues with only 4 of our users (out of ~60) and Outlook on desktop. While open throughout the day, at some point outlook displays the "Trying to Connect..." error on the bottom status area. Sometimes it doesn't present that error, but emails will start to stack up in the Outbox or you get the Send/Receive progress bar at the bottom that doesn't progress. Restarting the machine often works to resolve the issue, but no other fix has worked consistently. I've used the SARA tool on each of the machines and it progresses through to reestablish credentials and rebuilds the user profile, but that has only worked successfully on 1/4 computers. The other 3 would hang up when Outlook was trying to sign the users back in to load their profiles, no matter how many times I restarted or closed Outlook and reopened. Have tried on both wired and wireless connections. Windows 10 and Office updates are up to date. Have even tried turning MFA off with the same results. We are in a Hybrid AD configuration with mailboxes on Exchange, if that helps, though one of the users are straight Azure AD joined and still getting the same issue. What is going on here? 55/60 users are having no issues

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
4,905 questions
Microsoft Exchange Hybrid Management
Microsoft Exchange Hybrid Management
Microsoft Exchange: Microsoft messaging and collaboration software.Hybrid Management: Organizing, handling, directing or controlling hybrid deployments.
1,898 questions

4 answers

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  1. workforce45 626 Reputation points
    2022-11-10T17:28:04.147+00:00

    Hi Jeff,

    Kindly perform below-mentioned troubleshooting steps on affected machines. Please ensure that Outlook is closed while performing these steps.

    General Troubleshooting

    Clear/remove all temporary files from the temp folder.
    Perform a SFC purge cache using "sfc /purgecache" command in cmd-administrator.
    Perform Disk cleanup.
    Remove/uninstall unnecessary apps from programs and features.
    Scan the PC using Windows Defender and remove possible threats.
    Perform a SFC scan using "sfc /scannow" command in cmd-administrator.
    Perform a clean boot and test the system/application.
    Boot the machine in a safe mode and test the Outlook application.
    Test the system/applications by turning off the firewall.
    Try restoring the PC using the previous restore point. (If possible)
    Repair the machine using system recovery. (If possible, provided you should know as how to do that)

    Outlook specific troubleshooting, please follow these links to find relevant steps.

    Repair Outlook Data Files (.pst and .ost) (microsoft.com)
    Troubleshooting Outlook issues (microsoft.com)

    Should you have any question, kindly revert to this thread.

    Regards,
    CK

  2. KyleXu-MSFT 26,211 Reputation points
    2022-11-11T08:33:06.037+00:00

    @Jeff Richard

    You can also follow those steps below to narrow down this one:

    Try to modify "Computer\HKEY_CURRENT_USER\SOFTWARE\Microsoft\Office\16.0\Outlook\Profiles" to Profiles.old (This step will create a new Outlook profile, after testing, you could change this name back to Profiles), then open Outlook and reconfigure mailbox in new profile. Check whether this phenomenon gone.

    If this phenomenon still exists, I suggest you try to configure another mailbox on this computer and configure this mailbox on another computer. Observe for a while, check whether the issue is related to the mailbox or the client. It could help us for the next troubleshooting.

    If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".
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  3. Randall Wade 1 Reputation point
    2022-11-14T21:59:37.15+00:00

    I have been fighting the same intermittent problem with 1 mailbox out of 180. This problem has been occurring for a couple of months, perhaps. Upon launching Outlook, there is a 50/50 chance the mailbox will get stuck 'Trying to connect'.

    I have tried the following steps in various order and some multiple times (plus some other steps such as turning on and off firewalls, AV, cleanups, etc):

    • Deleted the Outlook Profile and recreated
    • Updated Windows and Office
    • Repaired Office
    • Uninstalled and Reinstalled Office
    • Ran SFC
    • Ran SARA
    • Ran Dell Hardware diagnostics

    Nothing resolves this issue. Some days Outlook will get stuck for 5 minutes, other times it will be hours. Rebooting the device often works, but sometimes not. There seems to be no rhyme or reason that coincides with the times it gets stuck.

    The only step we have not done yet is a full repair/reinstall of Windows.

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  4. Gopal Agarwal 401 Reputation points
    2022-11-16T09:08:32.783+00:00

    Hi @Randall Wade

    Sometimes the issue can be occurring due to Incompatible or faulty Outlook add-ins may prevent or disrupt Outlook connection with the Exchange server. Open the Outlook in the safe mode and recheck all the add-ins manually.