Gmail tightened the checking of attached documents
By increasing the security of the email services provided, Gmail tightened the verification of attachments. This is how Gmail seeks to protect its customers from dangerous email with malicious add-ons. About gaps in the OpenAction team read Julius Sewing, a security specialist, article.
Gmail rejects emails with attached PDFs
Because of this protection, Gmail does not deliver all the emails that have an attached PDF document with the OpenAction team. Most often, these are PDF documents that the systems generate automatically. Typically, this problem occurs when sending emails generated by systems. For example, your e-shop accounts are generated automatically and sent in PDF format. In this case, Gmail can reject such outbound mails and customers will not receive them.
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