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Slow outlook startup issue

Hello Experts ,

Recently we have a particular Outlook agent taking much longer to connect to the Exchange server when starting Outlook. As the issue is sporadic we have not identified the real process of how Outlook stalls for this user.After checking connection status by using CTRL right click on the outlook agent and testing if the server name resolves to the server we are using all seems fine.

However we noticed one strange behavior, when outlook started without any issues the certificate prompt screen comes up almost immediately. On the other hand when Outlook waits with a Trying to connect to Exchange message on the status bar , the certificate prompt takes a long time to come up and it is hidden behind the main Outlook screen. As the user is often waiting for the connection to finish they do not realize they have a prompt to answer.

Is there any causes to this that we can find and resolve ? What would be a recommended next step in determining the slowdown ?

Thank you for your advice in advance.
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Radweld
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Thank you for the answers Radweld,We appreciate your assistance.

Your suggestion to test this brings up 2 questions that only require 1 answer:

Would the encryption not be required for the server to communiate with the client ?
As in would the outlook not change to Disconnected if we take off the encryption ?

Cheers.
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Thank you for this we will schedule this during off hours and we'll post results of test. Cheers
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Experts tip was not the answer but helped to get to answer through elimination.