9 in 1 to 100

A new Engineering building containing 100 offices had just been completed. John was hired to paint the numbers 1 to 100 on the doors. How many times will John have to paint the number nine (9)?




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Use the digits from 1 up to 9 and make 100.

Follow the rules.
=> Each digit should be used only once.
=> You can only use addition.
=> For making a number, two single digits can be combined (for example, 4 and 2 can be combined to form 42 or 24)
=> A fraction can also be made by combining the two single digits (for example, 4 and 2 can be combined to form 4/2 or 2/4)

Question: how can we do this?

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There is a cryptic organization called Cicada 3301 that posts challenging puzzles online, possibly to recruit codebreakers and linguists.