# Encrypting attachment

**URL:** <https://community.ciphermail.com/t/encrypting-attachment/570>\
**Category:** Gateway\
**Created:** [August 9, 2017, 3:50pm UTC](https://community.ciphermail.com/t/encrypting-attachment/570 "2017-08-09T15:50:29Z")\
**Posts on this page:** 2\
**Page:** 1

<div class="post-metadata">

**Author:** ![Paul\_Bronson](https://avatars.discourse-cdn.com/v4/letter/p/8e8cbc/32.png) [@Paul\_Bronson](https://community.ciphermail.com/u/Paul_Bronson)\
**Post date:** [August 9, 2017, 3:50pm UTC](https://community.ciphermail.com/t/encrypting-attachment/570/1 "2017-08-09T15:50:29Z")

</div>

Hi,

Using OTP, when someone encrypts a message outbound and it has a PDF attachment, it doesn't get attached. Is that expected behavior?

Paul

---

<div class="post-metadata">

**Author:** ![martijn](https://dub1.discourse-cdn.com/flex017/user_avatar/community.ciphermail.com/martijn/32/127_2.png) [@martijn](https://community.ciphermail.com/u/martijn)\
**Post date:** [August 9, 2017, 4:04pm UTC](https://community.ciphermail.com/t/encrypting-attachment/570/2 "2017-08-09T16:04:52Z")

</div>

Is the sender using Mac Mail?

You might try to enable the advanced PDF options "Deep scan"

From release notes ([Email Encryption Gateway release notes - CipherMail Email Encryption](https://www.ciphermail.com/gateway-release-notes.html)):

"PDF encryption now supports deep scanning which scans the complete MIME  
message"

For more info see [https://jira.djigzo.com/browse/GATEWAY-89](https://jira.djigzo.com/browse/GATEWAY-89)

Kind regards,

Martijn Brinkers

> **···**
>
> On 09-08-17 17:50, Paul Bronson via Users wrote:
> 
> > Using OTP, when someone encrypts a message outbound and it has a PDF  
> > attachment, it doesn't get attached. Is that expected behavior?