Cron hasn't crashed again since yesterday but there has been some suspicious logging today 
7/12/2012 3:51:45 AM    Info        Task completed: DWAY_APPL (4919)
7/12/2012 3:51:45 AM    Info        Job completed: DWAYDev_0.5Min_SQL_Create_New_Subscriber_Login inactive
7/12/2012 3:51:47 AM    Debug   New client connected.
7/12/2012 3:51:47 AM    Err          Error AuthenticateAsServer, ex: The handshake failed due to an unexpected packet format.
7/12/2012 3:51:47 AM    Debug   Client: 4903c9c3-5b14-4ac8-a89a-db12ce99866b (192.168.200.73) has disconnected
7/12/2012 3:51:52 AM    Debug   New client connected.
7/12/2012 3:51:54 AM    Err          Error AuthenticateAsServer, ex: Received an unexpected EOF or 0 bytes from the transport stream.
7/12/2012 3:51:54 AM    Err          Cannot write to sslstream.
7/12/2012 3:52:04 AM    Info        Job started: DWAYQA_Config_01Min_SQL_Create_New_Subscriber_Login
7/12/2012 3:52:04 AM    Info        Task started: QA Static1 (4920)
7/12/2012 3:52:04 AM    Err          Cannot write to sslstream.
7/12/2012 3:52:04 AM    Err          Cannot write to sslstream.
Still not sure what is causing this trouble, so far I have only seen this problem on one of several servers.