Deutsche Bank has been trying to leave its troubled past behind for years. But the fines keep coming.

The US Federal Reserve slapped the German lender with a $186 million penalty Wednesday for failing to fix "unsafe and unsound practices" that it pledged to address as long ago as 2015.

The Fed found that Deutsche Bank has made insufficient progress since 2018 to tighten its anti-money laundering controls, improve customer due diligence and ensure compliance with sanctions, among other failures. The Fed had already fined the bank a total of $99 million in 2015 and 2017 over the same issues.

The fine was also linked to Deutsche's involvement in a money laundering scandal at Danske Bank Estonia.

In its order, the US regulator said that although "some progress" had been made recently, Deutsche Bank's US operations "remained exposed to heightened levels of compliance risk... including the risk of failing to detect money laundering activity or US sanctions violations."

It directed the firm to make "substantial" progress on the issues by the end of this year or risk additional penalties.

The action highlights that Germany's biggest lender still has ground to cover in its long-running effort to move on from regulatory breaches — including mis-selling toxic mortgage securities — which have led to more than $10 billion in fines since the 2008 financial crisis.

The bank has worked hard to clean up its image and revive its earnings in recent years, launching an $8.3 billion transformation program in 2019, which CEO Christian Sewing billed as a reinvention.

Deutsche's turnaround efforts have begun to pay off: the once-struggling lender reported its highest quarterly profit since 2013 in the first quarter.

In a statement Wednesday, Deutsche Bank said it had "significantly invested in controls" since 2019 and increased the size of its global anti-financial crime team by more than 25%, to over 2,000 employees.

It said the Fed's actions "reinforce the need to ensure we stand by our commitments" and added that it "was well positioned to meet our regulators' expectations."

In its order, the Fed said a "significant portion" of $267 billion in transactions that Deutsche Bank cleared for Danske Estonia involved "high-risk" customers. Deutsche Bank exited the relationship in 2015.

In November, Germany's financial watchdog BaFin threatened Deutsche Bank with a fine if it failed to take action on money laundering and terrorist financing controls.