Recent U.S.-Iran diplomacy centers on a preliminary memorandum of understanding reached after months of mediated talks involving Qatar, Pakistan, and others, with virtual or electronic signings completed by President Trump, Vice President Vance, and Iranian representatives such as Parliament Speaker Mohammad Bagher Ghalibaf. A formal ceremony is scheduled around June 19 in Geneva or a comparable venue, yet it remains structured around delegations and procedural steps rather than direct bilateral contact. No verified reports indicate plans for an in-person meeting or handshake between Trump and an Iranian official before the June 20 cutoff. Traders assign a 96% probability to “No” because the compressed timeline, reliance on intermediaries, and history of cautious, sequenced engagement create significant logistical and political barriers to an impromptu personal encounter. A last-minute shift in the signing format or an unplanned bilateral sideline appearance could still alter the outcome.