Use DirtiesContext Annotation in Spring Boot Test

This is working as designed. Spring Framework's test framework will, by default, cache contexts for possible reuse by multiple test classes. You have two tests with different configuration (due to @TestPropertySource) so they will use different application contexts. The context for the first test will be cached and kept open while the second test is running. Both tests are configured to use the same port for Tomcat's connector. As a result, when the second test is run, the context fails to start due to a port clash with the connector from the first test. You have a few options:

1. Use RANDOM_PORT
2. Remove @TestPropertySource from Test2 so that the contexts have identical configuration and the context from the first test can be reused for the second test.
3. Use @DirtiesContext so that the context isn't cached