The latest example came when Trump defiantly tweeted on Monday night that he wants to call his plan to stop travel from six Muslim-majority countries a "travel ban" and "not some politically correct term."
"That's right, we need a TRAVEL BAN for certain DANGEROUS countries, not some politically correct term that won't help us protect our people," he tweeted.
The message contradicts what White House spokeswoman Sarah Huckabee Sanders said just hours earlier to defend Trump after his early Monday morning tweets about the travel ban.
"I don't think the President cares what you call it, whether you call it a ban, whether you call it a restriction," Sanders said. "He cares that we call it national security." She later added, "I think that the President isn't concerned with what you call it."
Earlier on Monday Trump tweeted "People... can call it whatever they want, but I am calling it what we need and what it is, a TRAVEL BAN."
Those tweets undermine an earlier statement by Trump's communications team, and emphasize the struggle with communicating for a President who is known for his off-the-cuff ability to reach out to his followers directly on Twitter.
Advisers close to Trump acknowledge that what the President calls his immigration plan -- a travel ban, or worse, a "Muslim ban" -- matters to the likelihood that it gets past federal courts and the Supreme Court. The travel ban, which is now in its second iteration, has already been blocked multiple times in court, with some judges suggesting it's meant to discriminate against Muslims.
Trump's previous comments and tweets about the ban have already been used against the lawyers arguing on his behalf.
Early in the administration, White House press secretary Sean Spicer outright scolded reporters for labeling Trump's plan a travel ban.
"When we use words like travel ban, that misrepresents what it is," Spicer said during his January 31 press briefing.
Trump has also undercut aides by confirming details of stories that his communications team had tried to refute.
After The Washington Post
and subsequent outlets reported that Trump disclosed sensitive classified information in a meeting with two Russian operatives, Deputy National Security Adviser Dina Powell told reporters, "This story is false. The president only discussed the common threats that both countries faced."
But the following morning, Trump got onto Twitter and said he had an "absolute right" to share information about "terrorism and airline flight safety."