Document grouping to Oberfeldwebel Otto Caro serving with Kampfgeschwader 6, 51, and 152.

Certificate to Luftwaffe Long Service Award 4th Class. Issued on 5.4.1938. Signed by Generalmajor Ulrich Grauert, Knight's Cross with Oak Leaves winner. 

Certificate to Air Gunner's Badge. Issued on 5.4.1938. Signed by Generalmajor Robert von Greim, Knight's Cross with Oak Leaves and Swords winner as well as Pour le Mèrite winner. From 1945 Generalfeldmarschall of the Luftwaffe. 

Certificate to 1939 Iron Cross 2nd Class. Issued on 18.6.1940. Signed by General der Flieger Ulrich Grauert, Knight's Cross with Oak Leaves winner. 

Certificate to 1939 Iron Cross 1st Class. Issued on 4.6.1942. Signed by Generaloberst Alexander Löhr, Knight's Cross with Oak Leaves winner.

Certificate to Squadron Clasp for Kampfflieger in Bronze. Issued on 4.8.1941. Signed by Oberstleutnant Johannes Janzen.

Certificate to Squadron Clasp for Kampfflieger in Bronze. Issued on 4.7.1942. Signed by Major Wilhelm von Friedeburg.

Certificate to Squadron Clasp for Kampfflieger in Silver. Issued on 4.7.1942. Signed by Major Wilhelm von Friedeburg.

Certificate to Squadron Clasp for Kampfflieger in Gold. Issued on 4.7.1942. Signed by Major Wilhelm von Friedeburg.

Certificate to Krim Shield. Issued on 15.3.1943. Facsimile by Generalfeldmarschall Erich von Manstein.

Certificate to Wound Badge in Black. Issued on 29.4.1943. Signed by an Oberfeldarzt.

Furthermore three period time documents. 

Each certificate has three holes. Signs of use and age. Condition 2/2-.