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There were several problems to fix. 1) a bug in the JDK (1.7 up to 7_60): https://bugs.openjdk.java.net/browse/JDK-8023130 which we can work around by detecting buggy VMs and not trying to use inheritIO. 2) File<->URL conversion is platform dependent and we shouldn't make any assumptions. The problem in this case was that file URLs contain a ":" so they can 't be added to a path in UNIX, but on Windows you need the absolute path with the colon. Solution: use Files on the classpath for spring-boot:run. Hopefully also fixes gh-767