Why doesn't the recipient see my email attachment?

[Doctor Q]

I haven't been able to solve this ongoing problem, and I could use some suggestions.

I send someone email with a photo attached, e.g.,

Dear John Smith,

Here's a nice photo.

Doctor Q

​

They write back that they received my email but that there was no attachment. But I see the photo in the quote of their reply, e.g.,

Doctor Q,

I got your email but I don't see the photo. Did you forget to attach it?

John Smith

From: Doctor Q
Sent: Monday, November 11, 2024 12:00 PM
To: John Smith
Subject: Nice photo

Dear John Smith,

Here's a nice photo.

Doctor Q

​

It doesn't always happen, but it's happened with various email recipients. Does it depend on which OS they have, which email client they use, or how it's set up? Does it depend on how I attached the image? What can I do about it?

 

[Bigwaff]

It doesn't always happen, but it's happened with various email recipients. Does it depend on which OS they have, which email client they use, or how it's set up? Does it depend on how I attached the image? What can I do about it?

What email client and version and protocol (IMAP / POP) do you use? What email client and version and protocol (IMAP / POP) does recipient use? I'd start there. Have recipient check the web version of their email service. Does embedded attachment image display on web version?

 

[Doctor Q]

I'm using the latest Apple Mail app under the latest macOS, with IMAP and a gmail address. I never know what the recipients are using. One clue is that they are usually business recipients, not personal email accounts, so they could be subject to some kind of server-side filtering. But I know that the image isn't filtered out since I see it in their reply. Without knowing, I'd guess that some or all of these recipients are using Outlook for Windows. I'm trying to solve the problem without the help of these business contacts.

 

[Bigwaff]

In Mail, check menu Edit > Attachments .. make sure "Always Send Windows-Friendly Attachments" is checked.

 

[Doctor Q]

Thanks for remembering that setting. Yes, I've always had that option checked, so that's not the solution.

 

[Fishrrman]

This may or may not help.

Before "attaching" the pic, convert it into a "compressed archive" (".zip").
- have pic visible in finder
- CONTROL-click on the pic (or right-click on it) to bring up the contextual menu
- choose "Compress xxx" (xxx representing the file name).
- result is a "zip" file that might "get through" when the pic file won't.
- attach and send that...

No promises...

 

[Doctor Q]

I've found that sending a zip file does work, and I've used that trick when attaching the image itself doesn't work. But I'd still like to determine why an image doesn't always show up in the recipient's email display, in case I don't have to resort to workarounds.

 

[dwig]

I've found that sending a zip file does work, and I've used that trick when attaching the image itself doesn't work. But I'd still like to determine why an image doesn't always show up in the recipient's email display, in case I don't have to resort to workarounds.

I've encountered this, frequently with TIFFs. It seems that the receiver's server or email app is filtering attachments, likely an overly aggressive malware filtering. These days I avoid sending naked TIFFs and other non-web files and send them as ZIP archives instead.

 

[Doctor Q]

I've found that too, so I always send jpegs, converted if necessary from other formats. My example above represents a jpeg that the recipient couldn't see, yet it showed up where their reply quoted my message. I think that means that their display of the jpeg is suppressed, and that it's still in the message (not filtered out).

 

[Fishrrman]

Just a thought...
Perhaps the person to whom you're sending has his/her email set to "not view" attachments (unless they specifically download them)?

I'm thinking of the PC equivalent (if there is one) of Mail.app's "load remote content" button (which can be set in Mail.app's settings)...

 

[Doctor Q]

If they have a "load remote content" setting turned off, it would be odd for them to tell me that I forgot the attachment, since it would be the case for everyone who sent them something. But it's certainly a possibility worth considering.

I'll probably need to work with one of these recipients to learn their OS, mail app, and settings, and perhaps do some experiments. But since they've been business contacts, it would be awkward. At some point I hope to get a chance to investigate that way.