We are experiencing an issue when using the Attach to Email option in Adobe Acrobat Reader DC v20.006.20034.39303. When we use this and then attach 2 or more additional attachments the 3rd document is corrupt. It always has a size of 4kb. If you try to preview the 3rd attachment in Outlook the error states: This file cannot be previewed because of an error with the following previewer PDF Preview Handler. If you try to open it the error states: Adobe Acrobat Reader could not open "file.pdf" because it is either not a supported file type or because the file has been damaged. I have replicated the issue with Outlook 2016 and 2019. I can take the same three pdfs and attach them just through Outlook and they come through with no issues. I have uninstalled with Adobe Tools Cleaner, reinstalled, ran a repair, and tested on multiple computers. I have also removed anti-virus software but still having the same issue. As another test I installed Phantom Fox-It and I can send the attachments through that application with no issues. It appears to just be when sending via Reader. Any help would be greatly appreciated. Thank you.