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Logins to Office365 keep failing

philled

I have found for the last few weeks/months that I consistently have problems logging into Office365. The only place I have this problem is on my LAN behind my Sophos UTM 9. To be clear, this isn't a matter of incorrect passwords!

Login attempts are successful around 20% of the time. The other 80% the page waits and waits and eventually give me an error:

- In the bottom Chrome status bar I see "Waiting for https://outlook.office365.com/". This will keep going for approx 30-40 seconds and then I get a page saying

The outlook.office.com page isn’t working

outlook.office.com didn’t send any data.

ERR_EMPTY_RESPONSE
It doesn't seem to matter what browser I use (even Microsoft IE or Edge). I've tried googling for this but I've not really come up with anything. I'm suspicious it's something to do with the Sophos firewall and ports. I think I read somewhere something about Office365 requests needing to open additional ports, though why it works sometimes and not others I have no idea, and would this even be true for browser-based Office365?
Does anyone else have this problem? What can I do to fix it? Or troubleshoot it?


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  • 0

    I've got more info on this. I've just done a test where the logon attempt failed (as usual); I then connected my PC to a VPN (exiting in my home city) and tried to login again. It logged in faultlessly. Does that indicate that the problem is with my networking/Sophos UTM, or my ISP?

  • 0 in reply to philled

    Does #1 in Rulz give us any hints?

    Cheers - Bob

  • 0 in reply to BAlfson

    The thing that solved this for me seems to be using a VPN. My login never seems to fail if I access it over a VPN. I have no idea why that resolves it, but it seems to do the trick.

  • 0 in reply to philled

    Hi,

    Did you verified the steps that was suggested via ?

    Thanks

  • 0 in reply to sachingurung

    I don't see anything in the Intrusion Prevention or Application Control logs. I see entries in the Firewall log but I don't know how to interpret them and all the domain names are converted to IP addresses which makes it difficult to know which entries are related to the Office365 site. Also, it doesn't seem easy to paste the contents in without including all my IP addresses. I thought I could copy to Notepad, mask my IP addresses and then paste here but the lines from the Live Log don't even paste properly into Notepad. How do most people paste their log entries on this forum?

  • 0 in reply to philled

    If you're going through the Web Proxy, you can see both the IP and the URL for each request.  If that's not possible, then maybe having a Firewall Live Log open with your local IP in the Filter box (hit Enter after you type it in!) might tell you where you're having a problem.

    Alone among the logs, the Firewall Live Log presents abbreviated information in a format easier to read quickly.  Usually, you can't troubleshoot without looking at the corresponding line from the full Firewall log file.  You can copy and paste the corresponding lines from the log file.

    Cheers - Bob

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  • 0 in reply to philled

    If you're going through the Web Proxy, you can see both the IP and the URL for each request.  If that's not possible, then maybe having a Firewall Live Log open with your local IP in the Filter box (hit Enter after you type it in!) might tell you where you're having a problem.

    Alone among the logs, the Firewall Live Log presents abbreviated information in a format easier to read quickly.  Usually, you can't troubleshoot without looking at the corresponding line from the full Firewall log file.  You can copy and paste the corresponding lines from the log file.

    Cheers - Bob

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