Apple Mail on iPhone not forwarding images

This has been the case as long as I can remember, but when I forward emails with images, the images don’t get forwarded. Of course, I’m talking about the default mail app.

Instead, I get a blank box where the image should be located.

This has always been a sort of minor quibble, but today I had to forward an email with images, and I had to go into the Fastmail app to do it.

Searching the Internet, I found only Apple Discussions (discussions.apple.com) of others complaining about the same issue.

Certainly, I must be missing a setting. I can’t believe this issue has been around this long.

Is this happening when you email just one or two people, or to everyone when you send it to a group? There’s a chance it could be a problem, or a preference, on the receiver side. On your side, check to see that Load Remote Images is checked in your Mail settings.

Did this just start happening now, or did you upgrade to 14.7 recently? It could be a bug.

Sending very large images, or lots of multiple images in a message could cause problems.

Is this happening when you email just one or two people, or to everyone when you send it to a group? There’s a chance it could be a problem, or a preference, on the receiver side.

No. When I see the forwarded messages, the images are not there. I have loaded the images manually before I sent the message and see the images.

On your side, check to see that Load Remote Images is checked in your Mail settings.

It’s not checked. I don’t want to automatically download images since that’s used to track when you open the message. However, when I forward a message, I make sure the images were manually downloaded.

Did this just start happening now, or did you upgrade to 14.7 recently? It could be a bug.

Been happening for a long time. For multiple releases.

Is no one else having this issue? It doesn’t come up a lot. You normally don’t forward that many messages and when you do, they rarely contain images.

I’ve seen this happen for quite a long time with iOS Mail. Testing it just now there are some where iOS Mail asks if I want to include the attachments and others where it does not. Looking at the source view of the messages on my Mac, I don’t see any differences that could explain it.

All the messages I looked at were sent from the same iPhone using iOS Mail through a Gmail account. The order of the message parts doesn’t seem to matter, the size of the message (with or without the image) doesn’t seem to matter, whether the images are from the Camera Roll (have filenames like IMS_0408.jpg) or not (have filenames like image0.jpeg or image.png) doesn’t matter.

There are inline attachments and attachments to the email itself. For example, Outlook normally does attachments to the email itself while Mail in iOS inline the image in the message.

It affects the way the MIME encoding is done. When the attachment is on the email message itself, the message is not MIME encoded, but there is a MIME attachment as a separate part. If the images are inline to the message, the message itself is MIME encoded.

What I’ve noticed is that if the image is attached to the message, iOS Mail will ask if you want to include the attachment. However, if the image is inline, it won’t include the image when forwarded.

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I have a hunch you’re right or on the right track.

The real rub is that the message whose images will not include in the forward was created and sent by me and from an Apple device. Must have been my Mac or iPhone. From the “raw source”:

X-Mailer: Apple Mail (2.3654.120.0.1.13)

The images are encoded as multipart MIME:

--Apple-Mail=_4EC0EAC3-2EDC-4040-9CE9-DAEDEA302709
Content-Transfer-Encoding: base64
Content-Disposition: inline;
filename=IMG_0848.jpeg
Content-Type: image/jpeg;
x-unix-mode=0644;
name="IMG_0848.jpeg"
Content-Id: <F49BB485-2FA9-4470-8B68-C03D2FEA2D57>

Anyway, the fact that if I go to my Sent folder to find an email I composed in Apple Mail (the one whose source is cited above) and select Forward, that the message is unable to correctly perform this very basic c. 1970s function – including the attachments – on a message that it encoded itself is pretty horrible. The message just includes the text:

<IMG_0848.jpeg>

where the photo should be. I had to use the “Resend” feature and then “quote” the old content to get it to work.

Lame.

In iOS Settings → Mail under the heading “Composing” there’s a setting to “Include Attachments with Replies”. Could that be set incorrectly for you?

This looks exactly like a long-time bug I have seen for years with Apple Mail on a Mac. Certain types of servers are not able to accept certain types of files (mostly if not always image files) sent from Apple Mail. It goes through to others with no problems. It is a “drive you crazy” bug because the users have no idea the attachments existed (unless they were explicitly mentioned and are explicitly required, so you may never know anything went missing.

I had a lot of problems with certain publishers, and it was consistent. It just happened when I sent something to my sister’s work email, and she reported: “They are still embedded in the email, not as an attachment I can move.” This seems to be primarily occurring with work servers; two cousins had no problems with similar files sent to personal mail on Gmail or Yahoo.

Does anyone have any more insight into this bug?

I had an issue years ago where some attachments were being embedded and they were small and distorted. It seemed to happen a lot with one of my jobs and a couple of customers, and I would have to send attachments through different accounts. I think even once they gave me my own mail account I had the issue because I was sending through Apple Mail. I haven’t had that problem in years though probably because I don’t have that job or customers anymore. Sorry to hear the bug is still around. I’m sure I’ve got posts on it here somewhere, it was really frustrating as I would get yelled at by the job for sending distorted files when I really hadn’t!

Diane

Thanks. I have now confirmed that the problem occurs with Outlook as a mail client, at least for one person. I problems with clients not receiving images sent from Apple Mail for several years, but am not working the same clients now. I have posted a description at Image files sent with Apple Mail 16.0 can… - Apple Community

I have now confirmed that one of my clients using Outlook has also had photos and Powerpoints I sent from Apple Mail go missing, but can receive them when I send from my webmail.