I've been using the Chilkat library for several years in some of my projects (iOS and OS X). Recently I needed to update some of them, so I also updated the Chilkat library. However, with the updated Chilkat library (both SMTP and IMAP) it seems impossible to connect using SSL.

Here's the test code:

(void)testConnection {

CkoImap *imap = [[CkoImap alloc] init];

BOOL success;

success = [imap UnlockComponent: @"Anything for 30-day trial"];

if (success != YES) {
```
NSLog(@"%@",imap.LastErrorText);

return;
```
}

imap.AutoFix = NO;

imap.Port = [NSNumber numberWithInteger:993];

imap.Ssl = YES;

imap.StartTls = NO;

imap.SslProtocol = @"default"; // Tried all possible options
```
//  Connect to an IMAP server.
```
success = [imap Connect: @"mail.lekkerthuis.biz"];

if (success != YES) {
```
NSLog(@"%@",imap.LastErrorText);

return;
```
}
```
//  Login (never gets here)
```
success = [imap Login: @"MeAndMyself" password: @"myPassword"];

if (success != YES) {
```
NSLog(@"%@",imap.LastErrorText);

return;
```
}

}

It fails with:

2015-11-10 11:41:47.485 IMAP-Test[1008:32633] ChilkatLog:

Connect_Imap:

DllDate: Oct 29 2015

ChilkatVersion: 9.5.0.54

UnlockPrefix: Anything for 30-day trial

Architecture: Little Endian; 64-bit

Language: Cocoa Objective-C

VerboseLogging: 0

connectInner:

  connectToImapServer:

    hostname: mail.lekkerthuis.biz

    port: 993

    socket2Connect:

      connect2:

        connectImplicitSsl:

          clientHandshake:

            clientHandshake2:

              readHandshakeMessages:

                processAlert:

                  TlsAlert:

                    level: fatal

                    descrip: unexpected message

                  --TlsAlert

                  Closing connection in response to fatal SSL/TLS alert.

                --processAlert

                Aborting handshake because of fatal alert.

              --readHandshakeMessages

            --clientHandshake2

          --clientHandshake

          Client handshake failed. (3)

        --connectImplicitSsl

        ConnectFailReason: 103

      --connect2

    --socket2Connect

    failReason: 0

  --connectToImapServer

  connect failed.

--connectInner

Failed.

--Connect_Imap

--ChilkatLog

If I link the project with the 2012-version of the Chilkat library, it works fine.

Answer

    Here's the verbose log:
    2015-11-10 12:19:55.764 IMAP-Test[1262:62029] ChilkatLog:
  Connect_Imap(625ms):
    DllDate: Oct 29 2015
    ChilkatVersion: 9.5.0.54
    UnlockPrefix: Anything for 30-day trial
    Architecture: Little Endian; 64-bit
    Language: Cocoa Objective-C
    VerboseLogging: 1
    connectInner(625ms):
      connectToImapServer(625ms):
        hostname: mail.lekkerthuis.biz
        port: 993
        socket2Connect(625ms):
          connect2(625ms):
            hostname: mail.lekkerthuis.biz
            port: 993
            ssl: 1
            connectImplicitSsl(625ms):
              Clearing TLS client certificates.
              connectSocket(419ms):
                domainOrIpAddress: mail.lekkerthuis.biz
                port: 993
                connectTimeoutMs: 30000
                connect_ipv6_or_ipv4(419ms):
                  Single-threaded domain to IP address resolution
                  connecting to IPV4 address...
                  ipAddress: 95.97.108.163
                  createSocket:
                    Setting SO_SNDBUF size
                    sendBufSize: 262144
                    Setting SO_RCVBUF size
                    recvBufSize: 4194304
                  --createSocket
                  connect(1ms):
                    Waiting for the connect to complete...
                    myIP: 95.97.108.164
                    myPort: 50512
                    socket connect successful.
                  --connect
                --connect_ipv6_or_ipv4
              --connectSocket
              clientHandshake(206ms):
                The client cert chain is NULL.
                cacheClientCerts:
                  Cached TLS client certificates.
                  Client cert chain is NULL.
                --cacheClientCerts
                clientHandshake2(206ms):
                  readHandshakeMessages(201ms):
                    processAlert:
                      TlsAlert:
                        level: fatal
                        descrip: unexpected message
                      --TlsAlert
                      passiveClose:
                        error on socket shutdown.
                        socketErrno: 57
                        socketError: Socket is not connected
                      --passiveClose
                    --processAlert
                    Aborting handshake because of fatal alert.
                  --readHandshakeMessages
                --clientHandshake2
              --clientHandshake
              Client handshake failed. (3)
            --connectImplicitSsl
            ConnectFailReason: 103
          --connect2
        --socket2Connect
        failReason: 0
      --connectToImapServer
      connect failed.
    --connectInner
    Failed.
  --Connect_Imap
--ChilkatLog
(lldb)

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IMAP/SMTP SSL Problems

Nov 10 '15 at 06:20

Answer