The lawyer’s objection, coupled with his advice to seek approval from the Department of Justice, is a significant blow to Trump’s hope to promote the hastily devised plan before Election Day.

Robert Charrow, a political appointee who serves as the Health and Human Services department’s general counsel, warned in the memo that the plan’s timing and design could invite legal challenges, those officials said. For instance, Charrow cautioned health officials that moving forward with the proposed $7.9 billion plan — which would be paid for by dipping into one of Medicare’s trust funds, and which senior Trump appointees had hoped to tout in letters sent to millions of seniors this week — would spark concerns about inappropriately using federal funds so close to the election.

Meanwhile, Charrow and his office late last week instructed administration officials to seek guidance from the DOJ’s public integrity section, which deals with election crimes, before moving forward with the drug-discount plan. That has further stalled the plan as the health department waits for DOJ review, said two officials.