MicroStrategy Inc.'s most recent crypto spending spree should deliver another hit to the company's bottom line.

The Tysons Corner, Virginia-based enterprise software company said Monday that it purchased an additional 13,005 bitcoins for about $489 million in cash at an average price of about $37,617 per bitcoin. The news did little to slow a dramatic slide in the world's largest cryptocurrency, with prices slumping nearly 10 percent, to roughly $32,300.

As a result of the freefall, MicroStrategy may have to mark down the value of the bitcoins it just purchased. Accounting rules dictate that the firm will have to write down its holdings once the market value dips below the price at which it acquired the coin. Bitcoin touched an intraday low of $31,735 on Monday, meaning that MicroStrategy may incur a nearly $77 million charge, according to data compiled by Bloomberg.