Member Avatar for H2ofield

Hi,
I'm not sure if this is the correct forum, so please let me know if there is another one that is more appropriate for this question… I have a home office/business and I'm using MS Outlook 2007 for emails. I'm trying to send an email that has a particular PDF file attached. For whatever reason, the email won't reach its destination if this specific PDF is attached. However, if I remove the attached file and send, the email goes thru. I have successfully been able to send other PDF attachments, but not his one. So, to figure this out in some creative ways, I tried to send an email w/attachment through a Yahoo account online, just to see if it is my ISP (IP address with Time Warner) or the company who hosts my company website (network solutions). However, even with the Yahoo account I cannot get the email w/attachment to reach any destination.
I'm perplexed. This is just a product datasheet in PDF format. I have sent it to many customers before with no problem. Also, I have not changed anything recently to this file. Can anyone figure this out? I have attached the PDF file to this thread. Maybe someone can try to send it to see if they see the same problem.
By the way, I find some other product PDF datasheets that wouldn't go through when emailed. The only common denominator that I can see is that these files have the letter "V" in the file name. But, how could this be the cause?

VCC5H(3H)_RevB.pdf (55.27 KB)
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  • Latest Post Latest Post by ctk_satz

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Thread contributions from , and point toward a transient content-filtering issue. The practical goal is to isolate whether the file itself, the sender path, or client-side software is causing the block. The checklist below gives concrete, reproducible steps and evidence to gather so the root cause can be found and, if needed, reported to an administrator.

Quick tests to isolate cause:

  • Recreate/flatten the PDF (open in the authoring app and “Print to PDF” or export as PDF/A). That removes embedded scripting, forms or strange metadata that some filters flag.
  • Rename the file to a simple lowercase name with no spaces or punctuation (e.g., datasheet.pdf) and resend.
  • Compress the PDF into a non-passworded ZIP and resend; success there points to content-based filtering.
  • Compare file size with other PDFs that send successfully; very large files are often blocked.
  • Scan the PDF with up-to-date antivirus; for non-sensitive files, an optional public scanner can show if engines flag it (do not upload confidential documents).
  • Send the same attachment through a different SMTP provider (Gmail, another ISP) or from a phone on mobile data to separate sender-path issues from local-network problems.

Evidence to collect before contacting the mail host or recipient admin:

  • Full non-delivery report (NDR) text and the original message headers (the SMTP error code and server names are vital).
  • A reproducible timestamp and the exact filename and file size.
  • A file checksum so admins can search quarantine logs, for example:
certutil -hashfile "C:\path\file.pdf" SHA256
md5sum file.pdf

Workarounds and next steps: host the file behind a short-lived cloud link if secure sharing is acceptable, request that the mail provider search quarantine for the SHA256/filename, or re-export the PDF using a different PDF producer. If the problem is intermittent, it commonly indicates a temporary filter update or heuristic false positive; retaining the checksum and NDR text will speed resolution with the mail provider.

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Member Avatar for caperjack

wouldn't touch that attachment with a ten foot pole .

Member Avatar for H2ofield

The problem seems to have fixed itself. The emails are now going through. I must have had something to do with Network Solutions new filter.

By the way, there is nothing nasty about the attachment. Just a product datasheet created in Corel. I've been sending this and others for a number of years.

Member Avatar for ctk_satz

check the outlook settings whether is ther any filter...

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