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Adobe Attachment Disappearing When Sent to Outside Client

New Here ,
May 01, 2019 May 01, 2019

Hello Adobe Community,

First, I am posting this in the Adobe Community as word and excel attachments do not have this issue indicating that this could be isolated to Adobe.

Quick background, I am an IT Support Technician working for an engineering firm. Currently we have an employee with an Adobe Acrobat Pro licence running on a Windows 7 PC with Microsoft Office 2016 installed. As of right now they are having issues with PDF attachments disappearing after the email has been sent. However when they look back at their sent items it shows that attachment icon indicating that there was an attachment sent with the email. However the attachment does not show up in their Sent item either. The way they are attaching a PDF is dragging the file from our network into the email. They then double click the attachment to make sure they are sending the right one, close out of adobe, then hit send.

What I have done so far is disabled the Adobe Cloud and PDF maker add-ins in Outlook. I have also repaired their Adobe program along with completely uninstalling and reinstalling the Adobe application. I have double checked that all HTML format is enabled across all of Outlook. Plain text and Rich text is not a factor. All of these troubleshooting techniques have not resoled the issue. Hence why I am reaching out to you guys.

I look forward to hearing your input on the matter and any possible solutions to this issue. If you need any further clarification other info please let me know. Thanks!

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General troubleshooting
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LEGEND ,
May 01, 2019 May 01, 2019

The Outlook add-ons are not involved in sending emails.

Acrobat is not involved in sending emails once you are in Outlook.

HTML and RTF format are unlikely to have any impact.

Does it work if the file is local?

Does it work if the file is attached by clicking rather than drag?

Do other people using the same mail back end see the same problem?

What is the mail back end?

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New Here ,
May 01, 2019 May 01, 2019

Thank you for your response. I had the employee test to see if locally it made a difference and so far it has not seem to do so. Same went for clicking. Currently we use Exchange 2013 for our mail end. As mentioned internal employees do not run into this issue. The attachment sends without any hitches. The clients they have been sending to have Gmail and MSN accounts. I had them send it to a couple of my personal accounts like Gmail and AOL. They yielded the same result.

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May 01, 2019 May 01, 2019

As previously reported in this thread, no Adobe product whatsoever is involved with the process of attaching and sending PDF files from Outlook or for any other e-mail client for that matter.

Since you are having the issue only with external recipients, you might want to check your security settings for Microsoft Exchange to see whether there are any policies set to strip attachments based on file type or filename suffix. It is possible that you might be embargoing outgoing attachments at the Exchange Server level.

          - Dov

- Dov Isaacs, former Adobe Principal Scientist (April 30, 1990 - May 30, 2021)
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LEGEND ,
May 01, 2019 May 01, 2019

It seems to me most likely that this is happening on the Exchange Server, or possibly on the client's PC if it has security software that monitors the mail sent. I would focus on this, rather than the Adobe software which isn't involved at all in sending mail.

It doesn't seem to be related to the target email if it doesn't get into the Sent mail. Seems that the attachment is stripped early in the process, so no use looking further downstream.

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New Here ,
May 20, 2020 May 20, 2020
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Hi.. I to am an IT Support / Exchange admin who is running into the same issue. Windows 10 woth Office 365. When users try sending PDF files to External receipients, the recipients receive the email but the pdf has been stripped and replaced with ATT Files. I verified from an Exchange side that the files are not being stripped due to any policies. Once I disable the Adobe Plug-ins within Outlook, the issue goes away.

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