The V-2 is considered the first man-made object to cross into space.
German V-2 rockets were used offensively beginning in September 1944 with testing beginning in March 1942.
The V1 was a jet propelled bomb with wings; the V2 was a liquid fueled ballistic missile. Both weapons had poor guidance systems and could only be trusted to hit within a few miles of their targets. In desperation, the Nazis built 175 Reichenbergs (Fieseler Fi 103R) which was a V1 flying bomb with room for a pilot who could precisely hit any target. The pilot would not have survived. Germany fell before any of them could be used.