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SMTP alerts no longer working | UPS Management Devices & PowerChute Software

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SMTP alerts no longer working

Discussion in UPS Management Devices & PowerChute Software started by Jacob , 1/3/2019 8:09 PM
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Posted in: General

SMTP alerts no longer working

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  • Cobb

    Long post incoming....

    I have a few Smart-UPS RT 6000 RM XL systems on my network that I have configured to send email alerts via a user/mailbox hosted in Office 365. This was working great, however after installing another unit today, my settings no longer work (according to the APC E-mail Test, and the email not reaching my address). I also checked my previously installed units, and they are also receiving the same error now. I'm currently receiving this error: 

    Test e-mail failed; SMTP configuration error.
    Last Server Response
    220 2.0.0 SMTP server ready
    My previous settings that were working correctly in the past, were:
    SMTP Server: outlook.office365.com
    Port: 587
    Authentication Enabled (with a user/email with a real mailbox & password)
    Use SSL/TLS: If Supported

    These settings worked in the past, sending the alert from the specified mailbox to my address hosted within the same o365 org/domain.
    Troubleshooting today, I've updated the NMC FW from v6.5.0 to v6.6.4. Also tried changing SMTP servers to smtp.office365.com, different ports (25,465,587), and Use SSL/TLS settings with no luck. Tested DNS, used an internal server and then Google DNS to verify name resolution. I've also referenced the APC documentation hosted here: https://www.apc.com/us/en/faqs/FA164769/ , still no luck.
    I've confirmed that my firewall/web filter are not blocking this traffic. I also verified I can sign into this mailbox in o365 with the credentials provided within the Authentication settings on the UPS. 
    I've ran out of ideas moving forward to troubleshoot, and why I'm posting, hoping someone can point something out that I may be missing.
    Thank you in advance.
  • Cobb

    Oops. Forgot to mention that I have other devices on the same network (copier/scanners), using the same SMTP settings, that are currently functioning properly. These devices use a different o365 user. I even tried using that different account on the UPS, same error.

  • ipicKedawinna

    Hi Jacob,

    I am seeing the same issue and will be looking into this and debugging.

    I am not quite sure what we'll find yet but just wondering if you're willing to help test or debug if we need it? If so, we can work offline together on this.

    P.S. I am wondering if it has to do with this and any changes they made: https://docs.microsoft.com/en-us/office365/securitycompliance/technical-reference-details-about-encryption?redirectSourcePath=%252fen-ie%252farticle%252ftechnical-reference-details-about-encryption-in-office-365-862cbe93-4268-4ef9-ba79-277545ecf221 

  • Cobb


    Thank you for the response and confirmation of the issue. The o365 TLS change definitely came to mind when troubleshooting this, as we did have to make changes to our o365 setup/connectors to fully support TLS 1.2. We went through that process a few months ago, prior to the cut off date stated by Microsoft. I do know, that these alerts were working AFTER we made those changes for TLS 1.2, and this appears to be something that "broke" about 2-3 weeks ago. I initially contacted APC support about the NMC and if it supported TLS 1.2, and from the documentation provided, the AP9631 NMC card supports this encryption/protocol starting with FW v6.5.0. This is why I updated the FW to the latest release(I think) to v6.6.4 during my troubleshooting steps. Unfortunately, the FW update did not solve the issue, and outputs the same error message.

  • ipicKedawinna

    Hi Jacob,

    You by chance don't have access to look at connection logs or do a packet capture on this do you? With the cloud setup, I am not sure if that is really a thing anymore depending on if your O365 is cloud or on-premise and what it allows you to see or do.

    I don't in my environment either so wasn't sure if you did.

  • JJordan

    Figured I would post this in hopes of saving someone's troubleshooting efforts. 

    I have the exact same problem you described as well as the behavior it working previously and then suddenly stopped working.  I have been working on this for 4+ days and today a Wireshark captured revealed a "Bad Certificate" on the SMTP transmission.

    Here is the packet capture.  Bad certificate (In my case) on host  (smtp.office365.com).  I currently have an open Microsoft O365 case for this as well.  

    Angela I have a existing case open on this.  #  54986873.  I haven't updated this ticket with these findings yet because I am waiting to hear Microsoft's response on this.