Why is Outlook eating some of my attachments?

October 4, 2021 12:29 PM

I work on an HP laptop. Work uses zimbra webmail that I access via Outlook. I send a lot of pdf-attachments. But every week or two I press send and then I check my sent mail and the attachment is no longer there. WHY???

I thought I was going crazy. But no, I check every single email and once every week or so I can see it when I press send, but it's vanished when I check sent mail. My clients are starting to think I'm a hot mess.
None of my 30-ish coworkers have the problem!

It doesn't seem to be related to anything in particular. It happens mornings and afternoons, it happens when I open attachments before sending and when I don't. Sometimes one pdf is still there and the other is gone. Sometimes both are gone.
It possibly happens to jpgs and docs as well, but I more rarely send those, so not sure.

Help meeeeeee

posted by Omnomnom to Computers & Internet (8 answers total)

I do know that when someone sends me an attachment, and I reply to that email, the reply no longer has the attachment....attached. Which sometimes is okay, but other times I'm replying to the original person and need to copy someone else to show it to them, and I have to re-attach it to the email since I've started as a "reply" to the original email.

Is that maybe what's going on?

I've had to remind my boss about how Outlook works that way a few times
posted by EmpressCallipygos at 12:40 PM on October 4, 2021

Response by poster: Is that maybe what's going on?

No no, I'm aware of that.
I'm the one who adds the attachments in the first place.
posted by Omnomnom at 12:44 PM on October 4, 2021

Is there a file size limit or security setting (on your end or the recipients' end) that might be silently taking the attachments off for some reason?
posted by Schielisque at 12:53 PM on October 4, 2021

Response by poster:  Is there a file size limit

Nah, those files are all 2 MB max.
posted by Omnomnom at 12:54 PM on October 4, 2021

I've noticed that some files that look "suspicious" trip the Outlook security filters and get stripped in transit. I can't attach a python source file to a work email, for instance; I have to put it somewhere and send the recipient the path. Is it possible these emails either have scripting in them, or something that an overzealous filter might interpret as scripting?
posted by Alterscape at 1:03 PM on October 4, 2021

Response by poster: Is it possible these emails either have scripting in them, or something that an overzealous filter might interpret as scripting?

I doubt it, because when I immediately resend the same file it goes through just fine.
posted by Omnomnom at 1:06 PM on October 4, 2021

While you troubleshoot this issue it would probably be better to add a link inside the body of the email to download the attachment so you don’t have to worry about your clients never receiving the file. You could use Google Drive, Dropbox, or Zimbra (if that’s a service they offer) to upload the file and create a shareable link.

Does this issue occur if you login to Zimbra’s website to check your email rather than using the Outlook’s desktop app? That may be another work around. I would also double check that Windows is updated to the latest version.
posted by mundo at 7:52 PM on October 4, 2021

Just some things to try and see if you run into this via a certain workflow. Does it make a difference if you:
1. attach the file using the menus/buttons within the email window after starting to draft the email
2. drag/drop the attachment in to the email
3. right click on the file and select the option to send as an email attachment.
posted by tillwehavefaces at 5:29 AM on October 5, 2021