httpd.exe mod_ssl.so The operating syste m cannot run %1.

I was upgrading my development server (WAMP) from Apache 2.2 (x32) to Apache 2.4 (x64) today. Everything went smoothly and was working without special modifications, except the ssl_module mod_ssl.so. I’ve almost got mad, because server didn’t start.

My issue was httpd.conf: Cannot load modules/mod_ssl.so into server: The operating system cannot run %1.

httpd.exe -t
httpd.exe: Syntax error on line 162 of ../bin/apache/Apache2.4.4/conf/httpd.conf: Cannot load modules/mod_ssl.so into server: The operating system cannot run %1.

Usually error message tells you what to do or what’s wrong. But this one was very strange. This error occurred on the upgrade Apache from 1.x to 2.x. Because I couldn’t find any solution for upgrade from 2.2 to 2.4 I decided to upgrade the openSSL.

Eureka!
It was openSSL! I had openSSL x32, but Apache 2.4 (x64) requires x64 openSSL library and not x32 that I had.

The latest version of openSSL library is available here. Don’t forget to install Visual C++ 2008 Redistributables (x64).

New attempt returned the result I wanted

httpd.exe -t
Syntax OK
Summary
Article Name
httpd.exe mod_ssl.so The operating syste m cannot run %1.
Jernej Lekše

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