As tech valuations collapse to a fraction of where they were last year, executives likely have a few regrets. One is sure to be acquisitions done at the top of the market.

It’s always tempting when stock prices and private valuations are trading at stratospheric levels for company executives to choose that moment to expand through acquisition. But it can be exactly the wrong move, one whose flaws will become apparent as valuations fall. That’s most evident with Salesforce’s purchase of Slack last summer—at a price that was far above any other enterprise software deals of the past six years. Another poorly timed deal was checkout software firm Bolt’s $1.5 billion plan to buy crypto startup Wyre, announced in April, right before crypto prices collapsed.