Google's headquarters in London, U.K.
Photograph by Bloomberg via Getty Images
By Aaron Pressman
May 12, 2016

With shares of Apple sinking on Thursday, briefly dropping below $90 for the first time in almost two years, the stock market value of Google’s parent, Alphabet, has again moved ahead of the iPhone maker.

Apple’s value declined to $493 billion in midday trading on Thursday compared to Alphabet’s value of $498 billion, according to Yahoo Finance.

Shares of Apple, which have lost 14% so far this year, were down 2.6% to $90.08 in midday trading on Thursday. Alphabet shares, which have dropped 7% so far this year, were down 0.7% to $724.74 in midday trading.

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This the second time this year that Alphabet’s (goog) market cap exceeded Apple’s (aapl) , with the first shift occurring for a few days time in February after a strong Google fourth quarter earnings report.

Claiming the title of most valuable company on the stock market grants some bragging rights, but has also been a warning sign of future poor stock performance. Besides Apple, companies including Exxon Mobil (xom) and General Electric (ge) have stumbled after gaining the largest market cap crown.

Lately, Apple has been struggling to convince investors that its massive growth phase fueled by iPhone sales has not come to an end. Apple reported that its revenue shrunk 13% in the first three months of the year compared to the same period in 2015, the company’s first annual decline in revenue in 13 years.

Meanwhile, Alphabet has also worried investors, if to a lesser degree, with its big spending on business units that aren’t expected to become profitable for years, like self-driving cars and efforts to find a cure for cancer. The company reported bigger losses on those long term bets in the first quarter than investors expected.

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