# S/MIME message has been decrypted but sending encrypted! **URL:** \ **Category:** Gateway\ **Created:** [February 25, 2021, 5:49pm UTC](https://community.ciphermail.com/t/s-mime-message-has-been-decrypted-but-sending-encrypted/728 "2021-02-25T17:49:17Z")\ **Posts on this page:** 2\ **Page:** 1
**Author:** ![Andreas\_Studenski](https://avatars.discourse-cdn.com/v4/letter/a/f07891/32.png) [@Andreas\_Studenski](https://community.ciphermail.com/u/Andreas_Studenski)\ **Post date:** [February 25, 2021, 5:49pm UTC](https://community.ciphermail.com/t/s-mime-message-has-been-decrypted-but-sending-encrypted/728/1 "2021-02-25T17:49:17Z")
Hi Martijn, I investigated in this case just once more. My email client understands S/MIME as long ciphermail is offline and not decrypting opaquely encrypted Mails. So if I send encrypted and signed mails from Outlook directly into my inbox, everything is fine. Only if Ciphermail is decrypting, my email client can't read the mail anymore. Do you see a chance for upcoming versions of Ciphermail to decrypt opaquely encrypted signed mails into clear text signed mails or give somehow the configuration option? Best regards, Andreas [attachment.htm](https://community.ciphermail.com/uploads/short-url/5YVLtx2VUEUMcCvLdlFjaoZKqBs.htm) (5.91 KB) > **···** > > -----Ursprüngliche Nachricht----- > Von: Martijn Brinkers via Users \ > Gesendet: Mittwoch 24. Februar 2021 10:56 > An: users(a)lists.ciphermail.com > CC: Andreas Studenski \; Martijn Brinkers \ > Betreff: Re: S/MIME message has been decrypted but sending encrypted! > > Hi Andreas, > > My guess is that the emails are not encrypted by opaque signed. S/MIME > signing supports two types of encoding: clear text and opaque. With > opaque signed email you need a mail client which understands S/MIME > signed email. Unfortunately some email clients like for example Outlook > use opaque signing when the email is encrypted. After decryption the > resulting email is therefore opaquely signed. If you mail client does > not support S/MIME you will only see an attachment names smime.p7m. > > You can configure the gateway to remove the signature by enabling the > S/MIME advanced setting "Remove signature". This will then convert the > smime.p7m attachment to a normal email. > > Unfortunately at the moment this will remove the signature from all > S/MIME emails, i.e., also from the clear signed emails and not just > from the opaque signed emails. > > Kind regards, > > Martijn Brinkers > > -- > CipherMail email encryption > Email encryption with support for S/MIME, > OpenPGP, PDF Messenger and Webmail Messenger > > On Wed, 2021-02-24 at 09:48 +0000, Andreas Studenski via Users wrote: > > > Hi there, > > > > my problem exists for a longer period now. As more and more S/MIME > > crypted mails are incoming, situation is getting annoying. > > So I started solving the problem, unfortunately without success. > > > > I have internal domains (locality "internal") in ciphermail, S/MIME > > certficates including private keys are successfully imported, mail > > routing works, everything is running fine except one weird thing: > > > > When S/MIME crypted mails are incoming for my user they will be > > decrypted by ciphermail. Logfile is showing "S/MIME message has been > > decrypted." and "S/MIME signature was valid", but only crypted mails > > are arriving in my inbox. > > I have searched for ages now and checked the configuration many > > times. Also reinstalled the server. Problem stays the same. > > Ciphermail does not decrypt mails. > > > > Anybody knowing this problem? > > Many thanks in advance. > > > > Andreas ---
**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:** [February 26, 2021, 8:31am UTC](https://community.ciphermail.com/t/s-mime-message-has-been-decrypted-but-sending-encrypted/728/2 "2021-02-26T08:31:44Z")
Hi Andreas, > I investigated in this case just once more. > My email client understands S/MIME as long ciphermail is offline and > not decrypting opaquely encrypted Mails. So if I send encrypted and > signed mails from Outlook directly into my inbox, everything is fine. > Only if Ciphermail is decrypting, my email client can't read the mail > anymore. Then your mail client does not fully support S/MIME. An S/MIME opaquely (i.e., embedded) signed email does look similar to an encrypted email but it's not the same. > Do you see a chance for upcoming versions of Ciphermail to decrypt > opaquely encrypted signed mails into clear text signed mails or give > somehow the configuration option? We will investigate whether it is possible to convert an opaquely signed email to a clear signed (i.e., detached) email. It might be that this is not be possible without breaking the signature. Kind regards, Martijn Brinkers > **···** > > -- > CipherMail email encryption > Email encryption with support for S/MIME, > OpenPGP, PDF Messenger and Webmail Messenger > > On Thu, 2021-02-25 at 17:49 +0000, Andreas Studenski via Users wrote: > > > Hi Martijn, > > > > I investigated in this case just once more. > > My email client understands S/MIME as long ciphermail is offline and > > not decrypting opaquely encrypted Mails. So if I send encrypted and > > signed mails from Outlook directly into my inbox, everything is fine. > > Only if Ciphermail is decrypting, my email client can't read the mail > > anymore. > > > > Do you see a chance for upcoming versions of Ciphermail to decrypt > > opaquely encrypted signed mails into clear text signed mails or give > > somehow the configuration option? > > > > Best regards, > > > > Andreas > > > > \> -----Ursprüngliche Nachricht----- > > \> Von: Martijn Brinkers via Users \ > > \> Gesendet: Mittwoch 24. Februar 2021 10:56 > > \> An: users(a)lists.ciphermail.com > > \> CC: Andreas Studenski \; Martijn > > \> Brinkers \ > > \> Betreff: Re: S/MIME message has been decrypted > > \> but sending encrypted! > > \> > > \> Hi Andreas, > > \> > > \> My guess is that the emails are not encrypted by opaque signed. > > \> S/MIME > > \> signing supports two types of encoding: clear text and opaque. With > > \> opaque signed email you need a mail client which understands S/MIME > > \> signed email. Unfortunately some email clients like for example > > \> Outlook > > \> use opaque signing when the email is encrypted. After decryption > > \> the > > \> resulting email is therefore opaquely signed. If you mail client > > \> does > > \> not support S/MIME you will only see an attachment names smime.p7m. > > \> > > \> You can configure the gateway to remove the signature by enabling > > \> the > > \> S/MIME advanced setting "Remove signature". This will then convert > > \> the > > \> smime.p7m attachment to a normal email. > > \> > > \> Unfortunately at the moment this will remove the signature from all > > \> S/MIME emails, i.e., also from the clear signed emails and not just > > \> from the opaque signed emails. > > \> > > \> Kind regards, > > \> > > \> Martijn Brinkers > > \> > > \> -- > > \> CipherMail email encryption > > \> Email encryption with support for S/MIME, > > \> OpenPGP, PDF Messenger and Webmail Messenger > > \> > > \> On Wed, 2021-02-24 at 09:48 +0000, Andreas Studenski via Users \> \> wrote: > > \> \> Hi there, > > \> \> > > \> \> my problem exists for a longer period now. As more and more > > \> S/MIME > > \> \> crypted mails are incoming, situation is getting annoying. > > \> \> So I started solving the problem, unfortunately without success. > > \> \> > > \> \> I have internal domains (locality "internal") in ciphermail, > > \> S/MIME > > \> \> certficates including private keys are successfully imported, > > \> mail > > \> \> routing works, everything is running fine except one weird thing: > > \> \> > > \> \> When S/MIME crypted mails are incoming for my user they will be > > \> \> decrypted by ciphermail. Logfile is showing "S/MIME message has > > \> been > > \> \> decrypted." and "S/MIME signature was valid", but only crypted > > \> mails > > \> \> are arriving in my inbox. > > \> \> I have searched for ages now and checked the configuration many > > \> \> times. Also reinstalled the server. Problem stays the same. > > \> \> Ciphermail does not decrypt mails. > > \> \> > > \> \> Anybody knowing this problem? > > \> \> Many thanks in advance. > > \> \> > > \> \> Andreas