why does my Outlook refuse to send emails to certain addresses?

[gabagoo]

This is just to wierd, and I have no explanation for the customers.

It does not happen to often.

I am trying to send a layout to a customer, a pdf file 34 kb. First time I send it to his home...it gets bounced back with a mailer deamon. I then send it to his corperate address and the same thing happens.

I called him a few minutes ago and told him I cant seem to get the file to him, so he sends me and email, I open it and reply and attach the file, and now it just sits in the outbox and wont go. He then gave me someone else's email in the office and I tried that one, so now I have 2 emails sitting in the outbox.

I then emailed a friend and it sat in the outbox for about 15 seconds and then went, but the other 2 still remain.

I had this happen a few months back from of all places a Gov't of Canada email address. Now in both circumstances they tell me they have had no issues with receiving emails.

What does anyone think is causing this problem?

 

[gabagoo]

OH, I see one went and now the other quickly followed by this...

This message was created automatically by mail delivery software.

A message that you sent could not be delivered to one or more of its
recipients. This is a permanent error. The following address(es) failed:


So how does this happen and how does one remedy the situation?

 

[HaroldDesign]

I've had emails be rejected because the file was too large for what their server will allow, and I've had them be rejected simply because it was a native file and their server doesn't like it. Try zipping the attachments and see if they go through.

 

[ddarlak]

I had this happen twice.

Once it was my hosting service, they have a blacklist of places they will not send email to because the destination email had burned them with spam. Thats the hardest to fix. You have to contact the person who isn't getting the mail and have their IT guy contact the refusing provider and try and get themselves removed from the blacklist. This took about 6 months to work out. It wasn't until a few other people started telling them that their emails weren't going thru before they took action.

The second time it was my internet provider refusing to deliver the email. I can't remember how i got that solved. I do remember having to talk to multiple people at Time Warner/Roadrunner over a month's time before i got it to work.

Until then, I used an email account I have on yahoo to send the mail. Very much a pain in the a$$, but effective....

 

[gabagoo]

I had this happen twice.

Once it was my hosting service, they have a blacklist of places they will not send email to because the destination email had burned them with spam. Thats the hardest to fix. You have to contact the person who isn't getting the mail and have their IT guy contact the refusing provider and try and get themselves removed from the blacklist. This took about 6 months to work out. It wasn't until a few other people started telling them that their emails weren't going thru before they took action.

The second time it was my internet provider refusing to deliver the email. I can't remember how i got that solved. I do remember having to talk to multiple people at Time Warner/Roadrunner over a month's time before i got it to work.

Until then, I used an email account I have on yahoo to send the mail. Very much a pain in the a$$, but effective....

will try the internet email and see if that works

 

[Kentucky Wraps]

Check the size of your SENT folder. Is it over or close to 2 gigs? If so..that's the problem.
Soon as a folder is that size...you start having problems. I can't fit in the sent folder so it doesn't want to get sent. If that's not the case there are tons of other possibilities.