PDF Software causing problems in sending some PDF files but not all?

I have been having problems sending some emails with PDF attatchments, they are being returned more and more frequently. I've spoken to our server host and his answer is as follows saying that the problem is we are using "cheap PDF software" which is why I can send PDF's via Gmail or Yahoo but not through our server. He suggest we buy a more expensive software or using Gmail for our important bids and invoices that are sent daily.
My question is: Is this even close to what could be causing the problem. We are using Adobe to create our PDF's using our HP CM1410 or the Neat Scanner. The Neat is a new device but the problem was ongoing before the Neat Scanner was added.
Our IT person who set our network, hardware and software says it's the server and he's never heard of this being an Adobe problem. So we're stuck not knowing who to believe

There are several potential problems. It could be that your e-mail client is not encoding the PDF properly, but looking at it as an ASCII file (7-bit characters). The encoding is not as much of a problem anymore, but still a potential issue. The structure of the PDF that you are getting from the scanner may be corrupt. You can use some of the preflight scripts to check the integrity of the PDF. You might even try saving as a new PDF to see if the 2 versions work differently.
It might be better to print the proposals you mentioned to the Adobe PDF printer and get better quality proposals than you would get with a scan. That would also probably avoid the problem you are having.

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On 3G we cannot send Business emails from either our iPhones or Ipad and this also happens with some WiFi connections but not all. Yet we can always send emails from our Hotmail Account using both 3G and WiFi.
We bought the iPhones and Ipad so that we could send emails while we are out of the Office, but we are not able to do this unless we can find a WiFi connection. Incoming emails are fine. We use IMAP, for Business emails just incase this is relevant and I know that Hotmail is POP3.
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The final environment the PDF will be embedded into will be inside a web application deployed to an application server, so I guess my problem is solved.
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PDF Software causing problems in sending some PDF files but not all?

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