Apple has struggled for years to pull off big acquisition deals because of a series of quirks. That leaves investors questioning how the world’s most valuable technology company plans to use its $246 billion cash pile to meet ambitious sales targets and expand into new markets.

“We are always looking at acquisitions,” Apple CEO Tim Cook told analysts last month. “There’s not a size that we would not do.”

It’s a message he’s increasingly stressed over the past year as investors question how the world’s most valuable technology company plans to use its $246 billion cash pile to meet ambitious sales targets and expand into new markets, such as transportation.

But Apple has struggled for years to pull off bigger deals because of a series of quirks: an aversion to risk, reluctance to work with external advisers like investment banks, and inexperience in closing and integrating large takeovers, said people who have worked on acquisitions with the company.

They asked not to be identified speaking about private merger and acquisition deliberations.

“The first step in M&A is having some conviction about what it is you want to do,” said Eric Risley, managing partner at Architect Partners who has negotiated deals with Apple.

“Apple probably more than most feels that they’re very capable of building things” rather than buying them, he added. An Apple spokesman declined to comment.

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Apple’s biggest deal in its 41-year history was the $3 billion purchase of Beats Electronics in 2014, followed by the $400 million acquisition of NeXT Computer in 1996.

In Facebook’s 13 years, it has made three acquisitions of at least $1 billion, including its $22 billion WhatsApp purchase. Google, founded in 1998, has done four such deals, while Microsoft has completed at least 10, according to data compiled by Bloomberg.

Instead of closing big deals, Cook has so far focused on growing Apple’s services businesses, including Apple Music, the App Store and iCloud.

That’s beginning to work, with the company recently forecasting that annual revenue from those operations will top $50 billion by 2021.

Sanford C. Bernstein analyst Toni Sacconaghi recently said Apple needs at least one big acquisition in online video.

To reach its $50 billion target, the company must find an extra $13 billion in services revenue over the next four years — beyond what it can generate itself.

Netflix ended 2016 with sales of less than $9 billion, so even buying that business may not be enough, the analyst said.

Other potential blockbuster Apple acquisition targets include Walt Disney Co. and electric carmaker Tesla, Baird analyst William Power wrote in a recent note to clients.

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“They’re going to have to pursue something bigger than a Beats-like acquisition,” said Erick Maronak, chief investment officer at Victory Capital Management, which holds Apple stock among its $55 billion under management.

But so far, the company has tiptoed around the edges of some of the biggest transactions reshaping the technology industry.

When AT&T agreed to purchase Time Warner for $85 billion in October, the telecom company was concerned Apple might make a competing bid, people familiar with AT&T’s thinking said.

Apple had held tentative talks about a year earlier, but when the AT&T deal emerged, a person familiar with the technology giant’s thinking said it wouldn’t be able to pull together a competing bid quickly enough.

Last year, the company considered buying luxury carmaker McLaren Technology Group, people familiar with the discussions told Bloomberg at the time.

Apple also had takeover talks with chip designer Imagination Technologies Group, but said last year it wouldn’t make an offer.

Apple often refuses to work with investment bankers appointed by the seller, preferring to deal directly with company management, according to people who have been involved in such negotiations.

Apple also dictates terms and tells targets to take it or leave it, betting that the promise of product-development support later and the chance of appearing in future iPhones are alluring enough, the people said.

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Apple’s current M&A strategy works well for acquiring startups developing new technology that can be added to existing Apple products. It bought 15 to 20 companies per year over the last four years.

But buying larger companies presents a different challenge, particularly if there are rival bids. Bankers often diffuse tension between bidders and targets, but Apple’s approach can make that process difficult.

“There’s a swagger — you may call it arrogance — about the culture there,” said Risley, of Architect Partners. “They’re used to being able to muscle their way in and get attractive economics.”

Large acquisitions can also go wrong in big ways. After buying Nokia’s handset business for $9.5 billion, Microsoft had to write down $7.6 billion of that value in 2015.

Failures like that helped forge Apple’s caution on larger deals, according to one of the people familiar with its thinking.

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