@niebochod, with the help of your debugging, I was able to fix the issue on Windows where scripts were not starting when OH starts. Here is the PR…
https://github.com/openhab/openhab-core/pull/1367
This PR will end up in OH 3.0, but I’ve made a test jar that is built to work with OH 2.5.x. If you’d like to try it (or anyone using scripted automation with Windows!), use your console to uninstall this bundle…
bundle:uninstall org.openhab.core.automation.module.script.rulesupport
Then shutdown OH, download this jar, and copy the jar into your /addons/ directory. To test, restart OH and your scripts should start on their own.
If/when you clear the OH cache, like when updating OH, you will need to repeat these steps since the old bundle will be reinstalled and there will be errors due to also loading the test bundle. To remove the test bundle, delete the jar and clear the cache.