Looked at the logs you pasted. I found these errors appeared a few times in the log: 17:04:33|Warning| Error deleting file C:\Users\cobpad0\AppData\Local\Microsoft\MSCRM\Client\MetadataCache-8b1bcb58-2468-e911-8167-001dd8b71c16.sdf: The process cannot access the file 'C:\Users\cobpad0\AppData\Local\Microsoft\MSCRM\Client\MetadataCache-8b1bcb58-2468-e911-8167-001dd8b71c16.sdf' because it is being used by another process.. Marking it for the deletion upon the reboot. Basically MetadataCache-xxxxxxxx-xxxx.sdf is the local file which used to store the meta data. Seems the process can not access it for some reason. When you connect the Outlook Client to the org, the meta data from server side is also supposed to be written into this file. If for some reason this file is not accessible, the configuration of Outlook Client will fail since meta data will be read from this file in later stage. Could you please check two things? 1. Check the size of this MetadataCache-xxxxxxxx-xxxx.sdf, usually it should be dozens of megabytes 2. Check whether there is some local machine setting which may prevent writing into this file
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