Error: The request failed. The decryption operation failed, see inner exception

Error

The request failed. The decryption operation failed, see inner exception.

Error source

MigrationWiz.

Cause

This error occurs when connecting to some IIS servers from Microsoft Azure.

Resolution

  1. Confirm that the error text matches "The decryption operation failed, see inner exception". Similar sounding but generic TLS handshake failure or timeout error is a different issue with different causes and should not be treated the same way.
  2. Check the SSL/TLS certificate installed on the source IIS server and confirm it has not expired, that its subject/SAN matches the hostname MigrationWiz is connecting to, and that the full certificate chain (including any intermediate CA certificates) is installed on the IIS server, not just the leaf certificate.
  3. Confirm that TLS 1.2 is enabled on the source IIS server. If a proxy or load balancer terminates HTTPS connections, confirm that its externally accessible endpoint also supports TLS 1.2. For Exchange Server configuration instructions, see Microsoft’s Exchange Server TLS configuration guidance.
  4. If an appliance performs SSL/TLS inspection or termination, review its TLS configuration and logs for errors at the time of the failed migration. Include any findings in your support ticket if the issue persists.
  5. For Exchange migrations using EWS, test connectivity to the source server using the Microsoft Remote Connectivity Analyzer or the EWS connectivity test referenced in the Exchange migration guide. Review the results, address any reported failures, and rerun the test. Save the results for your support ticket if the MigrationWiz error persists.
  6. If the certificate, TLS configuration, and network path all check out, collect the exact timestamp of the failed migration item, the source server's IIS and Exchange version, and the certificate details, then open a support ticket, review How do I get support for MigrationWiz? BitTitan investigates this error on a case-by-case basis to determine the fix or workaround.
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