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This article provides troubleshooting steps for resolving SSL errors on Windows after upgrading from Checkmk 2.2 to version 2.3. |
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Problem
After upgrading the Checkmk agent on a Windows host from Checkmk version 2.2.0 to 2.3.0 and above, you may encounter an SSL error when trying to register an agent.
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Checkmk version 2.2 uses Python 3.10, which includes OpenSSL 1.1.1m. In contrast, Checkmk 2.3 ships with Python 3.12 and OpenSSL 3.0.11. With this version, OpenSSL has discontinued support for many deprecated protocols and configurations, including certificates lacking SAN (Subject Alternative Name) entries.
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Solution
The solution is to recreate the SSL certificates to include the SAN (Subject Alternative Name).
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