I’m trying to troubleshoot an issue my client is having. She is using classic Outlook (as part of the 365 subscription & desktop software) on Windows 11, and as of a few months ago, she has intermittent problems sending emails with attachments. When the problem happens, the attachment can be of differing types – Word docs, PDFs, etc. She can send one email with a specific attachment and it might go through, and then send the same one to someone else with a few extra words, and it won’t go through (stuck in Outbox, when no other mail is pending in there). So it’s inconsistent.

She uses a Gmail account and there is no pattern that I can see to whether her recipients are also Gmail, or any specific email provider, when they fail.

Things I have tried:

Quick Repair (this fixed it once for a few months, but this latest time it did nothing)Created a new profileVerified that email attachments are well below any size limit thresholdVerified that internet is working fine at the time of the failureVerified that other emails without attachments can send normally at the same timeDownloaded the latest update for MS 365 today (did not fix the issue)

This is a relatively new computer (she got it Feb 2024) and it’s clean of malware and doesn’t get used for much more than email and web browsing.

It’s frustrating enough that she is considering jumping ship to something like Thunderbird or similar, but before she does that I said I wanted to post about it here and see if anyone has seen this issue and has an idea of what else to try. Thank you

​I’m trying to troubleshoot an issue my client is having. She is using classic Outlook (as part of the 365 subscription & desktop software) on Windows 11, and as of a few months ago, she has intermittent problems sending emails with attachments. When the problem happens, the attachment can be of differing types – Word docs, PDFs, etc. She can send one email with a specific attachment and it might go through, and then send the same one to someone else with a few extra words, and it won’t go through (stuck in Outbox, when no other mail is pending in there). So it’s inconsistent. She uses a Gmail account and there is no pattern that I can see to whether her recipients are also Gmail, or any specific email provider, when they fail. Things I have tried:Quick Repair (this fixed it once for a few months, but this latest time it did nothing)Created a new profileVerified that email attachments are well below any size limit thresholdVerified that internet is working fine at the time of the failureVerified that other emails without attachments can send normally at the same timeDownloaded the latest update for MS 365 today (did not fix the issue)This is a relatively new computer (she got it Feb 2024) and it’s clean of malware and doesn’t get used for much more than email and web browsing. It’s frustrating enough that she is considering jumping ship to something like Thunderbird or similar, but before she does that I said I wanted to post about it here and see if anyone has seen this issue and has an idea of what else to try. Thank you  Read More

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