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  • Outlook unable to send emails, continuously gets blocked

    Posted on wdtyler02 Comment on the AskWoody Lounge

    Home Forums AskWoody support Microsoft Office by version Office 365 and Click-to-Run Outlook unable to send emails, continuously gets blocked

    Viewing 5 reply threads
    • Author
      • #2285910 Reply
      • #2285921 Reply
        AskWoody Plus
        • Also, repaired O365 using the online version, but no joy
        • Tested using O2013 on my other laptop, with no errors

        It seems like this is either an authentication error for my Outlook/O365, or my laptop is now tagged as an IP address that is spamming.

        • This reply was modified 1 month, 2 weeks ago by wdtyler02.
      • #2286096 Reply
        Paul T
        AskWoody MVP

        Adding all the calendar items caused an email for each to be sent. This looks like spam to MS.

        You need to convince them to give you a little more leeway until you fix their broken software.

        cheers, Paul

        1 user thanked author for this post.
        • #2287466 Reply
          AskWoody Plus

          Thanks, Paul.  I have contacted MS re my addition of the calendar appointments, but they claim it is a machine-specific problem, and not an account problem, even though I have been able to send emails in the past.  There have been no major additions to software in the last month that could have caused this issue.

      • #2286354 Reply

        Alas, it is only this laptop. I was able to send a few emails after unblocking, but now MS Accounts team say that there are no issues with my account and the settings have been triple-checked by the Outlook team.

      • #2287506 Reply
        Michael Austin
        AskWoody Plus

        Your experience would frustrate and might even anger me. Sorry you had to go through it and you had to step through the ridiculousness of enumerating your error codes and symptoms.

        My computers, too, are PCs on Windows 10 Home. I’d been an Outlook 2010 user via licenses to my local machines for around 9 years until yesterday. Three years ago I’d already stopped using Outlook 2010’s calendar and tasks because I’d switched to Google’s Calendar (and Tasks) to share calendars with friends and co-workers. That has been working fairly smoothly. On my PCs I can view my calendar through a web browser. On our iPhones we view our calendars via the Google Calendar app.

        Although I use Outlook as my mail client on my PCs, I also have my mail routed (forwarded) through Google Mail with three flavors of mail server settings for different mailboxes. When I travel I access my mail on an iPhone through the Google Mail app. Once Outlook receives the mail, it’s set to keep all mail locally on the PCs. I keep four separate, automatic PST file backups. Two in the cloud.

        I still sync my iPhone to Outlook’s contacts, which takes learned levels of geekage which even Apple became unwilling and incapable of supporting. But because I’m willing to fiddle with things like Apple’s Mobile Device Drivers, I’d been able to work through iTunes’ bennial recalcitrance in syncing with Outlook 2010. To my happy surprise Outlook 2019 synced easily with iTunes I use iTunes to back-up the OS on two iPhones.

        Yesterday I re-upped my Microsoft licenses to its “2019”, single-machine licenses which include Outlook. I didn’t want to subscribe to its subscription services because in the last 10 years Microsoft’s support has progressively worsened, and it’s hideously expensive and time-consuming.

        Finance, social and tech founder. My new, planet-wide talk show, Casual Saints, is happening.

        1 user thanked author for this post.
        • #2287700 Reply
          AskWoody Plus

          Thanks, SoulRider, for the advice.  I am frustrated, and will try your suggestions.



      • #2296375 Reply
        AskWoody Plus

        Hello all.

        An update.  I can finally send emails.  It took the Outlook and the Development Team for Outlook to provide a UserID specific fix.  I believe from the email header data that they have bypassed the anti-spam filters on the server.


        • This reply was modified 5 days, 14 hours ago by wdtyler02.
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