Cannot send email with attachments

Have you installed and run any "cleaning", "optimizing", "speed-up", anti-virus or VPN apps on your Mac?

Have you tried putting the attachment in a folder an adding the folder to the email?

Give this a try: boot into Safe Mode according to How to use safe mode on your Mac and test to see if the problem persists. Reboot normally and test again.

NOTE 1: Safe Mode boot can take up to 3 - 5 minutes as it's doing the following; 

• Verifies your startup disk and attempts to repair directory issues, if needed

• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)

• Prevents Startup Items and Login Items from opening automatically

• Disables user-installed fonts 

• Deletes font caches, kernel cache, and other system cache files

NOTE 2: if you have a wireless keyboard with rechargeable batteries connect it with its charging cable before booting into Safe Mode. This makes it act as a wired keyboard as will insure a successful boot into Safe Mode.

FranT wrote:

My recipients are not receiving my emails with attached pdf or Word doc attachments. Regular email with no attachments works fine and I can receive attachments. On my end the email with attachment shows it has been sent but my recipients are not getting an email from me. There is no error message.

FWIW, on Monday of this week I sent an email with a 44MB attachment and it went through fine.

Then they need to check their spam/junk folder.

FranT wrote:

It's not them--unless it's multiple "thems." No one is getting any emails from me that have attachments.

Then contact your email provider. And if you did then state what troubleshooting they had you do.

FranT wrote:

They have. Nothing there.

Then they need to work it out with their email provider.

Hello