Cannot Send PDF by Hotmail on Mac

[simonvee]

Hi,

- Just today the problem started. I cannot email PDF documents to people using my Mac (specifically HOTMAIL). I can send normal emails with text and even JPG but not PDF. The email bounces back and says "Your message wasn't delivered because the recipient's email provider rejected it when I include a PDF document.

- I used both Firefox and Safari on my Mac to go into Hotmail to send PDF. Both failed.

- However, on my Mac, I can send PDF with GMAIL. It works. Strange!!

- I am able to email PDF using HOTMAIL through my iPhone. I can do it "from scratch" by iPhone. Or I can do it halfway on my Mac, save it on draft, and then go into draft on my iPhone and send it from there and it works.

The only dots that I can link is PDF <---> Hotmail <---> MAC OS

Interesting but highly annoying at the same time.

 

[Raz0rEdge]

I'm confused, if the recipient's provider is rejecting it, nothing you do should matter. Your mail provider shouldn't matter, your device shouldn't matter. Unless you are sending the successful emails to other folks whose email provider isn't blocking PDFs.

Mail, at the lowest level, doesn't care about what is being sent or attached. It's usually filters on top of that that prevent certain types of attachments or whatever. For example, most email providers will not allow an .EXE (Windows executable) to be sent as an attachment as it's a huge security risk. Folks will end up ZIP'ping it up to avoid that issue.

However, PDFs generally aren't perceived to be risky like executables can be.

 

[simonvee]

I send PDF emails to my customers on a daily basis. I was able to send one last night. Today was when the problem started.

I tried emailing to my own email address on Mac. Got rejected. Works when I send it by iPhone.

 

[Raz0rEdge]

Are you using Mail.app or something else to send the emails? Have you tried logging into the webmail interface of Hotmail and see if that works?

 

[simonvee]

Yep. Both the mail app and safari on IOS works work sending PDF emails.

 

[simonvee]

Yep. Both the mail app and safari on IOS works work sending PDF emails.

You can try sending PDF on your Mac with hotmail. We’ll find out if it’s just my Mac.

 

[pm-r]

Yep. Both the mail app and safari on IOS works work sending PDF emails.

What size is the PDF attachment that won't get sent or delivered and is it within the email size limits for attachments?



- Patrick
=======

 

[simonvee]

Just a little of 100kb
Very small document

 

[simonvee]

All GOOD! After the OS X update today it went back to normal. Happy.