I hope I'm not being to cryptic here, but I'm trying to convey the basic issue without typing up a novel...

I'm using Outlook.com with custom domains...

From a domain email account, I could previously send to a particular person@domain; 
then this week I was not able to send to anyone in that domain;
I added the user(s) and eventually @domain to my safe senders list and I could send basic text emails, but none with attachments (we are only sending .pdf's) and the .pdf's are less than 300k.

Looking at 'view message source' of my bounce message from "*** Email address is removed for privacy ***"
The lines in the message that stand out to me are:
---------- START SNIP
Final-Recipient: rfc822;*** Email address is removed for privacy ***
Action: failed
Status: 5.5.0
Diagnostic-Code: smtp;550 permanent failure for one or more recipients (firstname.lastname@RecipientDomain.ca:blocked)
--------- END SNIP

***As of this writing, I'm having doubts that the recipient is receiving any of our emails, with or without attachments.  I just don't get a bouncback from the emails with out attachments.

As far as I can tell, both the sending and receiving domains are not on any sort of block lists; 
the recipient domain's email is hosted by barracudanetworks.com and they are not blocking the sending domain.
I can send to the recipient domain from another domain with out issues.

We are using the outlook.com via Internet Explorer or Chrome -  this is not via an email client such as Outlook.
How do I ensure that outlook.com for domains IS NOT blocking the ability to send to the recipient domain?
Can anyone shed any light?

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