Mac mail app won't send attachments with emails

I have been having the same issue, emails with attachments are being send fine, but the attachments are not being received by the recipients, however as far as mac mail is concerned they seem to have been sent. When checking my send folder, the emails have the attachments all there. I have turned off the Privacy settings, but this did not work either.

I do not know how to fix this or even where to start. Should this be unable to be resolved I shall have to move Microsoft!!

Same,

2020 MacBook Pro, once I updated to Ventura, I can no longer attach attachments to email....

I have a Mac Mini M2 Pro with Sonoma, running mail Version 16.0 (3774.200.91.1.1) the server is GMAIL, since this last version, I cannot send an attachment. This happens in both cases: by dragging the file to the edit section or using the icon to upload the file.

Once you include or drag the file, a message of "downloading" appears when you use the file upload and the box with "?" when you drag. When you send the file, the receiving party gets the mail without the attachment.

There was a similar case on Ventura last year, it was solved by an update version.

Does anybody have this issue?

Can’t help wondering why someone from Apple isn’t commenting on this thread? It’s obviously a common problem for many of us!

I keep awaiting replies to emails I’ve sent with attachments and after days with no reply I then check sent emails only to discover the email has not been sent! Grrr! Need to revert to Gmail which is more stable….

K_8H wrote:

I've been having issues sending emails with attachments from the Mac Mail app on my Macbook Pro (macOS Ventura 13.3.1).

I've tried both insert options available through the app - file/attach files and the paperclip icon, but to no avail. The text in the email will send, but any file that is 'attached' does not send. When I check the mail in the send folder the attachments are there and showing, but any/all recipients do not receive the files (images, PDFs etc).

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The only work around I've found is sending attachments through the web browser, which works fine but is not a long term solution for me.

hmmm....

not sure how you send an attachment through the web browser unless it is some on-line website you are referencing; however when you say can't send email attachment (?) would seem these are two different issues not related unless you can clarify(?)

I would start with turning off privacy settings in Mail—these new bells and whistles sure seem to cause some headaches

Open mail app select Mail>Settings>Privacy disable all:

Protect Mail Activity

Hide IP address

Block all remote content

ref: —Mail Privacy Protection on Mac - Apple Support

Use Mail Privacy Protection on Mac - Apple Support

If no resolve see:

—if you are using Hide My email—try disabling this feature and compare your results...

Set up and use Hide My Email in iCloud+ on all your devices - Apple Support

—if you are using iCloud Private Relay on Mac - Apple Support try disabling this feature and compare your results...

Use iCloud Private Relay on Mac - Apple Support

compare your results, reboot if necessary.

I will add —The current stable release of Ventura including bug fixes, security updates is macOS Ventura 13.4.1

Keep your Mac up to date - Apple Support

Keep your Mac up to date - Apple Support

Same with me,

I have a Mac Mini M2 Pro with Sonoma, running mail Version 16.0 (3774.200.91.1.1) the server is GMAIL, since this last version, I cannot send an attachment. This happens in both cases: by dragging the file to the edit section or using the icon to upload the file.

Once you include or drag the file, a message of "downloading" appears when you use the file upload and the box with "?" when you drag. When you send the file, the receiving party gets the mail without the attachment.

There was a similar case on Ventura last year, it was solved by an update version.

I worked this out in the end but with no help from Apple. To be honest I find the forums here frigging useless, lots of dumb techs suggesting ' Errr check you've upgraded your software' in a dumb arse voice. Of course that's the first thing anyone is gonna do after they've *icked around for an hour. There's a button called 'Include Attachments' in the tool bar. If this is switched off then the email won't send an email with attachments.

I've tried all of this, but the problem remains.

I have now updated my macbook to Sonoma 14.2.1, but nothing changes.

What else can I do? All I can do now is always to send emails using safari, but that is a huge loss of time!

I had this problem and solved it after I noticed that in my Mail toolbar at the top there was a button that is obviously accidentally pressed that denied me returning an email that had attachments. So I pressed it and voila the email then sent fine. I'm replying to this thread on my phone right now so can't recall exactly what the button was labelled as. I turned on customise toolbar and then removed it in order to avoid this stupid issue ever again. Hope that helps.

Using Sonoma Mail on Mac mini Pro M2: rules instructions not being followed. After simplifying such that all incoming emails are captured the accompanying pdf attachment is lost during forwarding rule.

Sonoma Mail is NOT RELIABLE email program at this point. Fortunately, but disappointing, is that I'm running Outlook for Mac v16.66 on previous system (2019 iMac27 running Catalina 10.15.7) in parellel until I can complete migration with confidence; seems it going to take awhile. Level of team incompetence working on Apple Mail seems implausible. Perhaps there is more going on here than I understand. I welcome input from anyone with solution.

So there's still no way to fix this? Or has anybody been able to solve it?

Have to agree, still an ongoing problem and yet radio silence from Apple...

Same issue as well with Mail attachments unable to send, on an MB Pro M2 running Sonoma.

Except there is no Include Attachments in the toolbar.

I am having this exact issue running Ventura and using Mac Mail client. Were you able to resolve this? Or did you end up moving to Microsoft :) ?