Round Brass with ribbon = War Merit Medal (Possibly genuine)
Cross with Swords in a Modern case = War Merit Cross with Swords (Possibly genuine)
Round Dark medal with ribbon = Russian Front medal (likely genuine)
2 small square flag pins = Winter Help(WHW)Donation pins (genuine)
2 rolled ribbons = Not WWII -origins unknown
Small eagle with swastika = origins unknown (Possibly genuine?)
"Much that once was, is lost. For none now live who remember it."
The medal in the box is a german ww2 Kriegsverdienstkreuz and the medal in the plastic pocket is the so called frozen meat order, real name Ostmedaille for those who served through the winter 1941 on the eastern front- whether they are original or not there are several people on this forum more skilled at determining this but neither medal is particularly rare. The KVK is with swords so it was given to a serving soldier. It would be ranked under the Iron Cross Second Class.
Please post them separately in their respective areas.
Searching for anything relating to, Anton Boos, 934 Stamm. Kp. Pz. Erz. Abt. 7, 3 Kompanie, Panzer-Regiment 2, 16th Panzer-Division (My father)