He won't follow instructions. After one meeting in which they urged Trump to steer clear of a certain topic, he sent a tweet about that very theme before they arrived back at their office. 

He won't compartmentalize. With aides, advisers and friends breezing in and out of the Oval Office, it is not uncommon for the president to suddenly turn the conversation to Russia -- a subject that perpetually gnaws at him -- in a meeting about something else entirely. 

And he won't discipline himself. Trump's legal team, led by Marc E. Kasowitz of New York, is laboring to underscore the potential risk to the president if he engages without a lawyer in discussions with other people under scrutiny in widening Russia inquiries, including Jared Kushner, his son-in-law and senior adviser. 

Nearly two months after Trump retained outside counsel to represent him in the investigations of alleged Russian meddling in last year's election, his and Kushner's attorneys are struggling to enforce traditional legal boundaries to protect their clients, according to half a dozen people with knowledge of the internal dynamics and ongoing interactions, who spoke on the condition of anonymity to discuss the matter candidly.

 Jared Kushner, son-in-law and senior adviser to President Trump, listens during session with cybersecurity experts at the White House in January. (Jabin Botsford/The Washington Post)

Compounding the challenges have been tensions between Trump's and Kushner's legal teams in a frenzied, siege-like environment. Senior White House officials are increasingly reluctant to discuss the issue internally or publicly and worry about overhearing sensitive conversations, for fear of legal exposure.