Scanning to e-mail via Office 365 woes

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  • ApeosMan
    Trusted Tech

    Site Contributor
    100+ Posts
    • Nov 2009
    • 183

    #1

    Scanning to e-mail via Office 365 woes

    I've set up scanning to e-mail via Office 365 around a dozen times successfully, the steps I've taken to get it to work are:

    1. Either use smtp.office365.com or their podXXXXX.outlook.com (xxxxx is their pod server number).
    2. Set the machine from e-mail and the SMTP authentication account to the same user.
    3. Set SMTP port to 587.
    4. Make sure STARTTLS (which is via port 587) is enabled as Office 365 uses TLS.

    These settings have always worked, but there is one customer which I'm having problems with, and I know it's not the MFP I'm using, as I've set up scan to e-mail via Office 365 with this MFP half a dozen times on the same firmware level. Anyway I'm getting server connection errors. The scanned job just sits there in the job queue on the MFP for several minutes before timing out. I believe that something is blocking port 587 outbound. I asked the customers I.T. rep and he checked and said nothing should be blocking it outbound or inbound. I also tried to scan back to my own personal e-mail via port 25 with no luck and my Gmail test account via port 465 (SMTP SSL) with no luck, once again I got connection timeout errors. The customers ISP appears to offer no mail server to use, grrr.

    Now the IP details on the MFP are correct and I can access the internet from the MFP too, as the meter capturing software on the device can easily access the internet and then onto the meter reading server via ports 80 and 443.

    I have a feeling that port 587 and by the looks of it 25 and 465 are blocked outbound by the ISP. I can understand port 25, but 587 and 465!!??? The ISP they use is a minor one and I can't find much info on it, so I may have to pass it onto their I.T. rep to investigate, but I prefer to investigate these things myself as often things get unfairly blamed on the MFP when it's not at fault.
    I did a telnet to smtp.office365 on port 587 and got no response, but on my home internet connection I got a response. So it appears as if port 587 is being block on the customers network or ISP level.

    Any thoughts, tips, advice etc would be greatly appreciated.

    Thanks
    Last edited by ApeosMan; 09-21-2013, 01:47 AM.
  • slimslob
    Retired

    Site Contributor
    25,000+ Posts
    • May 2013
    • 36834

    #2
    Re: Scanning to e-mail via Office 365 woes

    I have encountered both ports 25 and 465 being blocked by ATT to any SMTP server other than theirs. I haven't tried port 587. Try using port 80. A number of email services now can use port 80.

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    • MattL
      Technician

      50+ Posts
      • Apr 2012
      • 97

      #3
      Re: Scanning to e-mail via Office 365 woes

      The attached guide is from Sharp for scanning with Office 365 with their machines, might be a useful one to check.
      Attached Files

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      • ApeosMan
        Trusted Tech

        Site Contributor
        100+ Posts
        • Nov 2009
        • 183

        #4
        Re: Scanning to e-mail via Office 365 woes

        Thanks for the info Matt, all my settings are correct, as I've set scan to e-mail up via Office 365 up many times before, but that guide is helpful. I've come to the conclusion that there is nothing more I an do with this as it's on the customers end, something is blocking port 587 outbound, either on their network or ISP level. Just thought I'd add this comment to help others in the future with problem solving.

        I also did a test back to my latop which has a mail server on it to prove the MFP wasn't at fault.

        Comment

        • MattL
          Technician

          50+ Posts
          • Apr 2012
          • 97

          #5
          Re: Scanning to e-mail via Office 365 woes

          Often the case, go in one customer everything is allowed outbound, go to another and its so restricted, frustrating when they are not willing to work to fix something that will benefit them!

          Comment

          • TonerMunkeh
            Professional Moron

            2,500+ Posts
            • Apr 2008
            • 3865

            #6
            Re: Scanning to e-mail via Office 365 woes

            Another workaround is to scan to mail.messaging.microsoft.com, the only drawback is the customer can only scan within their enterprise domain.
            It's 106 miles to Chicago. We've got a full tank of gas, half a pack of cigarettes, it's dark and we're wearing sunglasses.

            Hit it.

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            • ApeosMan
              Trusted Tech

              Site Contributor
              100+ Posts
              • Nov 2009
              • 183

              #7
              Re: Scanning to e-mail via Office 365 woes

              Originally posted by TonerMunkeh
              Another workaround is to scan to mail.messaging.microsoft.com, the only drawback is the customer can only scan within their enterprise domain.
              Thanks what port is that on? It seems port 25 outbound and 465 are being blocked either on their network or ISP level with the customer I was having issues with.

              Thanks again for that info, it will be good to use elsewhere if needed.

              Comment

              • TonerMunkeh
                Professional Moron

                2,500+ Posts
                • Apr 2008
                • 3865

                #8
                Re: Scanning to e-mail via Office 365 woes

                It was 25 with no authentication.
                It's 106 miles to Chicago. We've got a full tank of gas, half a pack of cigarettes, it's dark and we're wearing sunglasses.

                Hit it.

                Comment

                • ApeosMan
                  Trusted Tech

                  Site Contributor
                  100+ Posts
                  • Nov 2009
                  • 183

                  #9
                  Re: Scanning to e-mail via Office 365 woes

                  Ok so I have a few customers who were successfully scanning to email via smtp.office365.com are now getting error codes saying 'un-supports smtp auth'. No settings have been changed on these Xerox MFP's. Strange thing is on Xerox MFP's that are a year or two newer we don't get this error. I'm thinking that Office365 have updated to a newer Authorization protocol or TLS version, but I can't find any info as to if this is true or not.

                  Has anybody else had this issue? It appears that it's only been happening in the last couple of weeks.

                  A last resort my be to get a wireshark capture to see what exactly is going on.

                  I can always use an alternate mail server as a work around, but I'd love to know what's going on.
                  Last edited by ApeosMan; 03-01-2014, 04:45 AM.

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                  • ApeosMan
                    Trusted Tech

                    Site Contributor
                    100+ Posts
                    • Nov 2009
                    • 183

                    #10
                    Re: Scanning to e-mail via Office 365 woes

                    Hmmm after doing some information searching it appears that Office 365 now requires TLS v1.1+ 256bit encryption. Their mail servers (behind smtp.office365.com) have been gradually updating to this standard since late last year. Hence why some of my customers were getting intermittent issues that got worse over time.

                    Looks like Microsoft didn't officially announce this either, which has annoyed some people.
                    Last edited by ApeosMan; 03-01-2014, 06:02 AM.

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                    • ApeosMan
                      Trusted Tech

                      Site Contributor
                      100+ Posts
                      • Nov 2009
                      • 183

                      #11
                      Re: Scanning to e-mail via Office 365 woes

                      TLS v1.2 with 256bit encryption is needed anything under TLS v1.2 shouldn't work.

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