Outlook 2016 Error 550 Permanent Failure: Delivery Failed - Microsoft Community

i had upgrade outlook pushed.

since when attach word/excel/powerpoint attachments outgoing emails, error reads "550 permanent failure: message delivery failed.  if believe message in error, please review user service agreement , contact support".

this happens regardless of email address trying send to.  

however can pdf files sent through email.  tested trying send word/excel/powerpoint attachment 1 recipient , got error each time sent pdf file same recipient , went through fine.  did same test various emails , everytime, pdf attachment goes through fine none of rest.

moved from: outlook.com / email /sending , receiving attachments

hello,

this issue might occur if have non-microsoft email address primary email address on account. let check on 1 following steps below:

1. sign in account https://account.microsoft.com/profile/.
2. select manage sign-in email or phone number.
3. select make primary next alias want primary. alias has microsoft email address such email account ends @outlook.com.

if still same, suggest clear cache , cookies of browsers. disable add-ins. many security programs includes "ad-blocking" protection. go through security programs running , check & disable ad-blocking feature, web blocking, etc. feature. you may try access email using different web browser.

once done, please try attaching files again.

let know result of suggested steps.

thank you.

Office / Outlook / Other/unknown / Office 2016