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Total nines written from 1 to 1000

Question

Writing every integer from 11 through 10001000, how many times in total do you write the digit 99? (A number like 919919 contributes two.)

Short answer

300300. Treat 00 to 999999 as three-digit strings: each of the three positions shows 99 in exactly 100100 of the 10001000 strings, giving 300300. The numbers 00 and 10001000 contain no 99s, so the answer is 300300.

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