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Strange problem with SMTP proxy and S/MIME certificates

apijnappels
On the UTM I configured the SMTP proxy and for one user I have imported the private key so the UTM can sign and encrypt messages.
When I use my laptop and configure it to use the UTM as SMTP server (with TLS and port 587)
I can succesfully send mails which are automatically signed and signatures check okay.

When I configure my Android phone with the same SMTP server settings mails get out, get signed but I get a message at the receiving party that the certificate is invalid.
When I do open the mail I can see it uses the same certificate which is correct. I suppose somehow the message gets changed after it has been signed, but I don't really know how to check this.
It doesn't make a difference whether I connect my phone by 3G or Wifi.

Anyone else seen this behavior of know where to look for any possible problems?


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    Attached I have the screenshots. Unfortunately they are in Dutch so I will try to translate where necessary.

    First picture says:
    "The digital signature of this message is invalid or not reliable"

    Second says:
    "it is possible that the content of the message has been changed. signed by arno... with RSA/SHA1"

    Last one says:
    "This message has an invalid digital signature. Open the message if you want more information."

    Managing several Sophos firewalls both at work and at some home locations, dedicated to continuously improve IT-security and feeling well helping others with their IT-security challenges.

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  • 0
    Attached I have the screenshots. Unfortunately they are in Dutch so I will try to translate where necessary.

    First picture says:
    "The digital signature of this message is invalid or not reliable"

    Second says:
    "it is possible that the content of the message has been changed. signed by arno... with RSA/SHA1"

    Last one says:
    "This message has an invalid digital signature. Open the message if you want more information."

    Managing several Sophos firewalls both at work and at some home locations, dedicated to continuously improve IT-security and feeling well helping others with their IT-security challenges.

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