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Questions tagged [smime]

S/MIME (Secure/Multipurpose Internet Mail Extensions) is a standard for public key encryption and signing of MIME data.

291 questions
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Different S/MIME signature between OpenSSL and C#

I'm trying to use an OpenSSL code in my .Net program. Here's the code: openssl pkcs12 -in "My PassKit Cert.p12" -clcerts -nokeys -out certificate.pem openssl pkcs12 -in "My PassKit Cert.p12" -nocerts -out key.pem smime -binary -sign -signer…
Arian Sharifian
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PKCS #7 SignedData issue in bouncycastle

I there! I have a problem with an openssl generated smime file. I need to parse (with the help of BouncyCastle) an smime SignedData package, generated with openssl. I used this command to create an example: openssl smime -sign -inkey…
ccoutinho
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Raw RSA decryption/signing

I'm implementing RSACryptoToken, that is an interface for RSA cryptographic tokens, according to the documentation. There are twp methods, called decryptRSA and signRSA - they should be implemented. In documentation there is an info, that they…
Taras
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Python's email package from the standard library inserts spurious linebreaks after S/MIME boundaries which seems to break S/MIME signing

I'm trying to use the cryptography library to sign a document. The following script (working.py) works when it is executed from a directory that contains a private key and a certificate: #!/usr/bin/python import sys from cryptography.x509 import…
pek
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Does decryption using BouncyCastle has a file size limit?

I'm new in cryptography and my scala code is not able to decrypt a file sized over 1.6Gb, i'm getting a BadPaddingException and it decrypt successfully with files sized less then that. I know that smime decryption using openssl cli has a limit size…
khalilosgh
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How to programmatically read and send encrypted emails using an Office 365 mailbox?

We are about to integrate an external message handling system with an Office 365 mailbox. When sending emails clients sometimes like to use the encrypt function provided by Outlook and expect the replies to be similarly encrypted. That is why we…
Malk
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encrypting an email using an EC X509 certificate

I'm trying to use BouncyCastle's SMIME package to create an encrypted message using ECDSA X509 certificates. According to BouncyCastle's release notes, this has been supported since 1.32 (I'm using 1.46), but I keep getting an exception stating…
senecaso
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Openssl asn1 encoding routines problem - decrypt p7m to xml

I'my trying to decrypt a P7M file in a XML file using openssl, command line: openssl.exe smime -inform DER -verify -in fattura.p7m -out fattura.xml With this command openssl is unable to decrypt a P7M with EIDAS signature (I think is this the…
wikimt
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Openssl wrong content type while decrypting signed and encrypted SMIME message

I have the following smime message of multipart body. I am trying to decrypt it with the openSSL command below, using a certificate and a private key. However I get an error of wrong content type. Does anybody know where this error comes from and…
mastersom
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X.509 certificate difference between S/MIME and HTTPS (LetsEncrypt)

Looking at LetsEncrypt FAQ page, they have clearly stated that email encryption and code signing require a different type of certificate and therefore they are not supported by LetsEncrypt. My understanding is that https and S/MIME both require…
Meisam Emamjome
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How to apply S/MIME certificate to Outlook programatically (Windows, C/C++)

We wish to automate the process of applying a S/MIME certificate to Outlook so that it can be used for Signing and Encrypting of email. We want to be able to programmatically set security setting preferences for: the signing & encryption certificate…
Tim de Haas
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Using S/MIME or PGP - are the single attachments hashed/signed?

I just had a discussion about integrity of S/MIME and PGP. I wonder if the different parts (eg attachments and body) are signed/hashed/fingerprinted separately or is this only applied to the resulting container? I checkd some RFC and websites and it…
Volker
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Signing S/MIME content from Python

I've tried various approaches to signing an email message using Python. There's the M2Crypto library mentioned here but that library no longer builds / works properly with Python 3.4+. There's a newer library cryptography which works well for…
tuck1s
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Difference between PGP and SMIME

I am wondering why is there a need for two secure email standards. If I am not completely wrong, nowadays PGP and SMIME essentially provide more or less the same functionality. In the past, the difference was that PGP build on a web of trust,…
Andrew
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S/mime signed and encrypted email adding signature to end of attachment

The text file attached to the email is received with additional characters which I believe is the signature and the email client says the email is not signed. Should I be using an AlternativeView for both the signature and the encryption? Have I…
Alan S
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