How do you embed images (JPEG) into an Apple Mail message so it REMAINS embedded in Gmail, instead of images becoming attachments?

jeffsyrop wrote:

No, Omnis is hosting my own website and email, zenhell.com.

Then that is the most likely culprit. Your original screenshot is from the gmail web interface, correct? Can you confirm that it looks correct inside Mail in your "sent" mailbox?

If so, then it is likely the email service. I did a quick check of Omnis and this web page says:

Important information about specific attachments: as a security measure to prevent potential viruses, Omnis doesn't allow you to send or receive executable files (such as files ending in .exe). Executable files can contain harmful code that might cause malicious software to download to your computer. You can't send or receive the following file types: .exe, .com, .bat, .scr, .pif, .cmd, etc, even in ZIP or RAR archives. In case of blocking, you will see a message like: "Virus scan failed: Omnis.ExecutableFileBlocked.Zip_exe FOUND".

And I think that confirms it. They are scrambling your outgoing e-mail. Here's a dirty little secret if you didn't already know. Internet services can do one of two things well - either web services or e-mail service. Nobody does both well. These days, I'm not sure anyone can do either. I have noticed a remarkable decrease in basic competency with respect to shared web hosting providers. 15 or 20 years ago, you could have some company host your website and e-mail and there was never any problem. That's simply not possible anymore. They just can't seem to manage it.

I'm moving all my sites over to AWS CloudFront. I have some peculiar requirements with language support, but I've figured out a way to get it working the way I want for the most part. Most people wouldn't have this problem. You can use AWS Lightsail just to get your feet wet with a VPS-style service. I'm getting tired of dealing with the SSL certificates. They are quickly going the way of the web host. I much prefer the free, one-click AWS certificates.

For e-mail, I use Office 365 because I can use my own domain. You can even do that with iCloud now. There are a handful of email service providers that offer comparable services. But the same rules apply. People who do e-mail well couldn't do a web site to save their lives. I would have said the opposite for people who do web hosting but no one seems to be able to do that anymore anyway, so it's a moot point.

Gmail shouldn't be affecting how users you send your emails to see them. Two things that can, or will, though:

1. They have their email client set to always display incoming messages as text.
2. Some email clients don't like that Mail uses rich text, but prefer HTML for mail that includes images, or other layout styling.

Gmail has nothing to do with what you're seeing. It's a mail server, which has no affect on how any email client works.

Apple's Mail app used to do what you want. Then for a while it started dropping all image attachments at the bottom. I did a test just now under Ventura 13.1 and Safari 16.2. I dragged and dropped two JPEGs into the editing window, along with some text. It now once again places images inline (embedded) with the text.

This worked as expected regardless of whether I had settings under composing set to rich, or plain text.

Kurt Lang wrote:

Some email clients don't like that Mail uses rich text, but prefer HTML for mail that includes images, or other layout styling.

Apple Mail hasn't used rich text for many years. This battle is long lost. Everything is HTML now.

jeffsyrop wrote:

Thanks. That sounded like it might be the key, but this is how my email was set up when I conducted the test this morning:

It is interesting that your "Send Windows-Friendly Attachments" setting is disabled. Perhaps whatever is controlling your Mail formatting is also scrambling your attachments.

This is a huge problem for me and must be for others.

I've never heard of anyone complain about this problem before. In fact, it is much more common for people to complain about the way that you want Mail to work, which is the way it works for everyone else.

Are you sending from a gmail account? Can you try sending from an iCloud or other account instead? While I have a gmail account, I never use it. I think the only time I've ever used it was just now to see if I could reproduce your problem, which I can't. I see that Google has been dutifully sending me spam every day since forever. Ah, what I've missed!

But regardless, I do not have gmail configured to work with Apple Mail. I tested sending from my Exchange account and my iCloud account and both worked fine, as viewed in the gmail web interface.

Your screenshot does have a hint. It says "Scanned by gmail" with a little "info" icon that you may be able to click on. It sounds like you have some "security" software configured that is interfering with the normal operation of Apple Mail and/or your gmail account. My guess is that this software is running locally on your Mac, but I'm not familiar with gmail so don't quote me on that. But it is quite likely that an antivirus app would disassemble your e-mail message, scan your attachments for viruses, and then reassemble it incorrectly.

From what I understand, Mac antivirus software is the only protection that Windows users have against virus-lade e-mails.

That wouldn't surprise me. I couldn't see how rich text would even work in email, but had to presume, "Well, that's what they say it is." Email clients like Outlook wouldn't know what to do with actual rich text.

I did a check of my really old sent mail. Apparently, Apple Mail has only ever sent out HTML mail.

Here is a sample from 2022:

--Apple-Mail=_F3FC54B1-A017-4E94-AEF0-591F4814B49B
Content-Transfer-Encoding: 7bit
Content-Type: text/plain;
	charset=us-ascii

This is a test of rich text

--Apple-Mail=_F3FC54B1-A017-4E94-AEF0-591F4814B49B
Content-Transfer-Encoding: 7bit
Content-Type: text/html;
	charset=us-ascii

<html><head>
<meta http-equiv="Content-Type" content="text/html; charset=us-ascii"></head><body style="word-wrap: break-word; -webkit-nbsp-mode: space; line-break: after-white-space;" class="">This is a test of <b class="">rich</b> text<br class=""></body></html>
--Apple-Mail=_F3FC54B1-A017-4E94-AEF0-591F4814B49B--

I did manage to find some actual rich text. Check out the MIME boundary header on this:

--Cyberdog-MixedBoundary-011BB5C9
Content-Type: text/enriched; charset=US-ASCII
Content-Transfer-Encoding: 8bit
X-Fontfamily: Geneva
X-Fontsize: 12

That's 22 years ago.

Haha! I was going to do the same test, but had turned my Mac off and was sitting here on my iPad reading a magazine.

There's the proof I was expecting to find - HTML headers. Odd that it would also include rich text.

Kurt Lang wrote:

There's the proof I was expecting to find - HTML headers. Odd that it would also include rich text.

No. It's only HTML. I had to dig into my old Cyberdog e-mail from the last century to see anything that wasn't HTML.

Circa 2008, there were Terminal commands to control how Apple Mail displayed attachments.

I have no idea whether they still work almost 15 years later.

If you'd like to try, triple-click on the boldface text line desired, Command+C to copy, and Command+V to paste it into the prompt of an open Terminal window. There were other revisions of these terminal commands using 'true' or 'false', but I found it was easier to remember that in binary 1='on', and 0='off'

The command to disable in-line attachments (attachments appear as icons)

defaults write com.apple.mail DisableInlineAttachmentViewing 1

To command to enable (and re-enable after disabling) in-line attachments (attachments appear as documents displayed in-line)

defaults write com.apple.mail DisableInlineAttachmentViewing 0

kostby wrote:

Circa 2008, there were Terminal commands to control how Apple Mail displayed attachments.

That only ever modified how attachments were displayed in an outgoing message. It never made any change to the format of the message.