File not found when sending email with attached pdf file

R

richw

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Exchange Server
Operating system::    Win 11
Outlook version:     365 desktop
Email type or host:    Exchange or 365 ?
I occasionally have to reply to an email and insert a pdf file. This always used to work. Now I get a "File not found" error and won't send the reply. When I click on the attachment it opens fine, so I assume it's there. Any ideas? Thanks.
 
When you say "insert a pdf file", do you mean that, from the Reply Main Menu, you are doing Insert -> Attach File?
Do you have problems attaching other file types? (e.g. plain text files)
 
Hornblower409 said:
When you say "insert a pdf file", do you mean that, from the Reply Main Menu, you are doing Insert -> Attach File?
Do you have problems attaching other file types? (e.g. plain text files)
Click to expand...
Yes. I'll get an email requesting a document. I'll scan the required doc and save it as a pdf file. Then reply to the requesting email using Insert -> Attach File. I have attached the file from the recents section in File Explorer (easiest) or from drilling down to the actual file location. Either way loads the file as an attachment and opens fine when ctrl clicking to check if it is actually there. When I click send is when I get the "file not found" error and won't send the email.

No problem attaching and sending a txt file type.

UPDATE: After attaching and sending a txt file without any problem, I tried another pdf file and now that worked as expected. I have no idea what is going on. I'll keep investigating when I have some free time.
 
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