SSL Handshaking Error in Windows Server while using Jira Cloud

 

Signs showing you might be dealing with this error:

  • Constant “System.Net.Http.HttpRequestException: An error occurred while sending the request. ---> System.Net.WebException: The request was aborted: Could not create SSL/TLS secure channel. ” Error in the logs.

  • You are using Jira Cloud

  • Connecting to https://tfs4jira-ondemand.spartez-software.com/tfs4jiraod/rest/synchronizer?url=https://{{YOUR_ATLASSIAN_DOMAIN_NAME}}.atlassian.net&myVersion={{VERSION_OF_SYNCHRONIZER}} does work in Chrome but does not work on IE on the machine hosting Synchronizer throwing message :

    Error message: “Turn on TLS 1.0, TLS 1.1, and TLS 1.2 in Advanced settings and try connecting to again. If this error persists, contact your site administrator.”

Solution number 1:

 Most of the time the problem is caused by there is no match between the set of cipher_suites supported by the machine hosting Synchronizer and the set of values that our server was able to accept. 

  1. Open the Registry Editor.

  2. Go to HKLM/SOFTWARE/Policies/Microsoft/Cryptography/Configuration/SSL/0010002

  3. Check if you have there any of those values:

    TLS_DHE_RSA_WITH_AES_128_GCM_SHA256 TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 TLS_DHE_RSA_WITH_AES_256_GCM_SHA384 TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 TLS_ECDHE_RSA_WITH_CHACHA20_POLY1305_SHA256

It needs to have at least one of them as those are cipher suites used by our infrastructure. If none of them is present add one (do not forget about making the backup of the registry!) and reboot the machine.

Solution number 2:

  1. Download and install IISCrypto

  2. Go to the Cipher Suites tab:

     

  3. Check if you have checked any of those ciphers:

    TLS_DHE_RSA_WITH_AES_128_GCM_SHA256 TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 TLS_DHE_RSA_WITH_AES_256_GCM_SHA384 TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 TLS_ECDHE_RSA_WITH_CHACHA20_POLY1305_SHA256

If not, check it and reboot the machine.