First, run the second encrypted text through the Playfair Cipher and you get "UNETWENTYSEVENTHNINETEENFOTQYFIVEX"

This tells you the date needed for the next part, June 27th

Go to an enigma machine emulator

For the setup, use the settings for June 27th

M4, B, Beta, II, I, VIII, A T Y F (found in InnerSettings.jpg)

16/2 25/21 6/20 9/17 22/1 15/4 18/26 8/23 3/14 5/19 T C X K (found in OuterSettings.jpg) (LetterNumber Cipher.jpg should help)

The numbers from OuterSettings.jpg each represent a letter in the alphabet (A is 1, B is 2, etc)

These are put into the plugboard, so that P goes in B, Y goes in U, etc

Finally, put the ciphered text into the input box and decipher, you get THEF LAGI SMAT HISO N

The Flag is Mathison