iCloud for Windows Outlook plugin is offline after PC sleep - causes errors

Every time I wake my PC from sleep, the iCloud icon in the Outlook ribbon shows "Go Online", meaning it is offline, instead of "Refresh" which is what it shows when connected. The PC reconnects to internet automatically on waking, but iCloud in Outlook does not.


This can lead to errors - creating a new iCloud calendar item in Outlook before remebering to click "Go Online" will result in a duplicate of the item in Outlook, but only one (after going online) synced to the cloud. The duplicate cannot be deleted on the PC, and it is necessary to sign out of iCloud completely, then sign back in, re-downloading everything from the Cloud, to get it right.


I have seen this issue posted by others before. It is not unique to my PC.

Windows, Windows 10

Posted on Jan 15, 2023 5:47 PM

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Jan 17, 2023 12:51 PM in response to Taycan2020

Hey Taycan2020,


We'd be happy to help out. If you're not able to reconnect automatically when waking from sleep for your iCloud for Windows Outlook add-in, we'd suggest working through the following steps:


1. Open Outlook as an Administrator. Right-click the Outlook icon in the "All Apps" section of the Start menu, select More then choose "Run as administrator"

2. Go to File > Options > Add-in's > Add-in's.

3. Select Go next to Manage at the bottom of the window. Highlight the iCloud Outlook Add-in, note the exact location of the .dll file which is shown in the "Location" field.

4. Select "Remove"

5. Select "Add" and go to the location of the .dll file, the location you have noted, left click the file then select "OK".

6. Re-check the iCloud Outlook Add-in" and "OK".

7. Re-check the "iCloud Outlook Add-in" and "OK" then restart Outlook normally.


We hope these steps help out with getting things working again as expected, but if they don't, you can contact Microsoft for further support on their product here: Microsoft 365 Support


Thanks for using Apple Support Communities.


Take care!


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iCloud for Windows Outlook plugin is offline after PC sleep - causes errors

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