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Internet Related/Filtering/Firewall Thread, O365, Outlook and secure connection delays in Technical; ...
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    bodminman's Avatar
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    O365, Outlook and secure connection delays

    Argh!

    We’re having some issues here connecting to Exchange Online (O365) via the Outlook client.

    When hitting ‘Go’ after entering all the credientials during the initial start up of Outlook, it spends ages on the ‘Search for blah@blah.co.uk server settings then delivers a message saying that ‘An encrypted connection to the mail server isn’t available….’ So I then try the unencrypted option which eventually just says that that can’t connect either.

    Even when doing this on a totally unfiltered machine we are having this issue.

    So the next step for me was to run the Packet Monitor on our Sonicwall box and I have discovered that at some point during the packed exchanges, there becomes a 30 second delay. Capture.PNG

    This is similar to the delay we have when connecting to outlook.com/blah.co.uk if we have ‘Check for server certificate revocation’ enabled in IE Advanced Settings. Which results in an extremely slow connection to Outlook and a very buggy experience when you do eventually do get logged in.

    Anyone got any ideas on resolving such issues? I’m thinking I maybe should gather a the logs for both of these issues and open a support call to MS!

    Thanks

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    zag
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    Proxy issue most likely.

    Try it on your home machine just to compare speeds. I suspect it will be very fast.

    We fixed this by running a transparent proxy for the initial setup.

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    bodminman (10th January 2014)

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    bodminman's Avatar
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    This happens even when plugged into the DMZ with a non domain laptop. Weird!

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    MS have been having connection issues with Outlook clients today, but it should be fine by 13:30 once they have applied the patch

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    bodminman (10th January 2014)

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    bodminman's Avatar
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    I shall try again this afternoon then and let you know how I get on!

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    bodminman's Avatar
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    Right, I still can't get this working!

    I have been in touch with MS Support and they say that as they can connect Outlook to our test O365 account then it's clear that the issue is internal here. Fair enough!

    So now I'm totally confused! I have had Sonicwall remoting into our Router and they're saying that the issue isn't with their box as it's all configured correctly!

    Losing the will to live with this!!!

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    zag
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    Have you tried it from home yet? Any difference?

    What about turning off the proxy for Office 365 sites?

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    bodminman's Avatar
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    I have just remoted my home PC and Outlook works fine.

    I have also just plugged in a non-domain laptop into the DMZ on the router and Outlook failed to connect.

    I think I shall be giving gSonicwall another call!

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    @bodminman did you manage to fix this please?

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    Quote Originally Posted by FN-GM View Post
    @bodminman did you manage to fix this please?
    Hi @FN-GM,

    The initial workaround was to untick the 'Check for server certificate revocation*' within IE Settings/Advanced. When I done that, everything worked.

    After further investigations, it turned out that some machines were still holding onto the settings for our old proxy server! (netsh winhttp show proxy)

    On these machine I just run 'netsh winhttp reset proxy' and once the bulk were done I reset the 'Check for server certificate revocation*' back to being checked.

    All now works a treat.

    HTH

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