(SQL Server) Send Encrypted Email using RSAES-OAEP with AES-128 CBC and SHA256

Demonstrates how to send encrypted email using RSAES-OAEP with SHA256 and AES-128 content encryption.

Note: This example requires Chilkat v9.5.0.67 or greater.

Chilkat ActiveX Downloads ActiveX for 32-bit and 64-bit Windows

-- Important: See this note about string length limitations for strings returned by sp_OAMethod calls.
--
CREATE PROCEDURE ChilkatSample
AS
BEGIN
    DECLARE @hr int
    -- Important: Do not use nvarchar(max).  See the warning about using nvarchar(max).
    DECLARE @sTmp0 nvarchar(4000)
    -- This example requires the Chilkat API to have been previously unlocked.
    -- See Global Unlock Sample for sample code.

    -- Load an RSA-based certificate.
    -- (Encrypting an email only requires the public key.  Decrypting an email requires the private key.)
    DECLARE @cert int
    -- Use "Chilkat_9_5_0.Cert" for versions of Chilkat < 10.0.0
    EXEC @hr = sp_OACreate 'Chilkat.Cert', @cert OUT
    IF @hr <> 0
    BEGIN
        PRINT 'Failed to create ActiveX component'
        RETURN
    END

    DECLARE @success int
    EXEC sp_OAMethod @cert, 'LoadFromFile', @success OUT, 'qa_data/rsaes-oaep/cert.pem'
    IF @success <> 1
      BEGIN
        EXEC sp_OAGetProperty @cert, 'LastErrorText', @sTmp0 OUT
        PRINT @sTmp0
        EXEC @hr = sp_OADestroy @cert
        RETURN
      END

    DECLARE @email int
    -- Use "Chilkat_9_5_0.Email" for versions of Chilkat < 10.0.0
    EXEC @hr = sp_OACreate 'Chilkat.Email', @email OUT

    -- Create a simple email.
    EXEC sp_OASetProperty @email, 'Subject', 'Sample RSAES-OAEP Encrypted Email'
    EXEC sp_OASetProperty @email, 'Body', 'Sample RSAES-OAEP Encrypted Email'
    EXEC sp_OASetProperty @email, 'From', 'support@chilkatsoft.com'

    -- Add a recipient.
    -- (The email is encrypted using the recipient's certificate.
    -- If sending to multiple recipients, then the AddEncryptCert method would
    -- need to be called once for each recipient's certificate.)
    EXEC sp_OAMethod @email, 'AddTo', @success OUT, 'Chilkat GMail', 'chilkat.support@gmail.com'

    -- Set the email object properties to indicate the desired encryption.
    EXEC sp_OASetProperty @email, 'Pkcs7CryptAlg', 'aes'
    -- If AES-256 is desired, set the following property to 256.
    EXEC sp_OASetProperty @email, 'Pkcs7KeyLength', 128
    EXEC sp_OASetProperty @email, 'OaepPadding', 1
    -- Other choices for the OAEP hash algorithm are "sha1", "sha384", and "sha512"
    EXEC sp_OASetProperty @email, 'OaepHash', 'sha256'

    -- Provide the certificate to be used for encryption
    EXEC sp_OAMethod @email, 'AddEncryptCert', @success OUT, @cert

    -- Don't forget to indicate that the email should be encrypted when sent..
    EXEC sp_OASetProperty @email, 'SendEncrypted', 1

    -- The mailman object will do the RSAES-OAEP encryption when sending.
    DECLARE @mailman int
    -- Use "Chilkat_9_5_0.MailMan" for versions of Chilkat < 10.0.0
    EXEC @hr = sp_OACreate 'Chilkat.MailMan', @mailman OUT

    -- Set the SMTP settings for your email account on your mail server.
    EXEC sp_OASetProperty @mailman, 'SmtpUsername', 'SMTP_LOGIN'
    EXEC sp_OASetProperty @mailman, 'SmtpPassword', 'SMTP_PASSWORD'
    EXEC sp_OASetProperty @mailman, 'SmtpHost', 'MY_SMTP_DOMAIN_OR_IP'
    EXEC sp_OASetProperty @mailman, 'SmtpPort', 587
    EXEC sp_OASetProperty @mailman, 'StartTLS', 1

    -- Send the email.  The mailman will encrypt the email as directed by the 
    -- property settings of the email object.
    EXEC sp_OAMethod @mailman, 'SendEmail', @success OUT, @email
    IF @success <> 1
      BEGIN
        EXEC sp_OAGetProperty @mailman, 'LastErrorText', @sTmp0 OUT
        PRINT @sTmp0
        EXEC @hr = sp_OADestroy @cert
        EXEC @hr = sp_OADestroy @email
        EXEC @hr = sp_OADestroy @mailman
        RETURN
      END

    EXEC sp_OAMethod @mailman, 'CloseSmtpConnection', @success OUT
    IF @success <> 1
      BEGIN

        PRINT 'Connection to SMTP server not closed cleanly.'
      END


    PRINT 'Mail Sent!'

    -- -----------------------------------------------------------
    -- This is an example of an RSAES-OAEP encrypted email
    -- -----------------------------------------------------------

    -- MIME-Version: 1.0
    -- Date: Thu, 27 Apr 2017 08:43:32 -0500
    -- Message-ID: <772DC039F0259C474BAC60240EA2BA2272402308@CHILKAT13>
    -- Content-Type: application/pkcs7-mime; name="smime.p7m"; smime-type="enveloped-data"
    -- Content-Transfer-Encoding: base64
    -- X-Priority: 3 (Normal)
    -- Subject: Sample RSAES-OAEP Encrypted Email
    -- From: support@chilkatsoft.com
    -- To: "Chilkat GMail" <chilkat.support@gmail.com>
    -- Content-Disposition: attachment; filename="smime.p7m"
    -- 
    -- MIICWQYJKoZIhvcNAQcDoIICSjCCAkYCAQAxggGgMIIBnAIBADB1MGgxCzAJBgNVBAYTAlVTMQsw
    -- CQYDVQQIDAJJTDEQMA4GA1UEBwwHV2hlYXRvbjEhMB8GA1UECgwYSW50ZXJuZXQgV2lkZ2l0cyBQ
    -- dHkgTHRkMRcwFQYDVQQDDA5DaGlsa2F0V2lkZ2V0cwIJAMRwugDmvniwMBwGCSqGSIb3DQEBBzAP
    -- oA0wCwYJYIZIAWUDBAIBBIIBABr0E1dKJjK0FAYRz/NCtJmBeB0nUxgcuBnhGPI/UeyGub3cCo+K
    -- G5F4/iVTBJqVvYIF5+fvBnyTginwv7OiUiFWLyihiFC3NIyZJO22+XMHpNatCffTPZk10WswkTgk
    -- G3ApnRvGQAaldnFD0Hs8drPU4vBvY9QsjT7YDGa6u2NMX+sr1ewEZArqU0mNfJ6RsEYd5FQbFEVF
    -- qLmnz8Dt+yhoJlUtfUd8TXIeqHRJ7RxKOTSzlBZaAdTv2QX4oL9IcAgZeTg5iw+yRPkSAwWyg+I/
    -- 7fybLsUpRGDHTGUU+AvHvP0kYKa1mkvccBVEC/+4hEyhpS1tWIR5ByY6vM76Z+8wgZwGCSqGSIb3
    -- DQEHATAdBglghkgBZQMEAQIEEKqD0YDHX1NsVDaV32UczpeAcLteQyRPTV4hATjwcPiVelPfeWNs
    -- xZKRGaEBqLM8+Y+V4ciCFoOlgJuOcP4m1PTHyilfzd+SCsKz5l1C7+sfPf36n2aacX6IWga59Bz5
    -- QbWrOHDUT7O5PnGwKVgQFw3Cj4GrdPGWKcoqxB0HuKnj3WA=

    EXEC @hr = sp_OADestroy @cert
    EXEC @hr = sp_OADestroy @email
    EXEC @hr = sp_OADestroy @mailman


END
GO