Background: Transvenous lead extraction (TLE) should be completed, even when facing difficulties which have yet to be described. The aim was to explore unexpected TLE obstacles (the circumstances of the occurrence and influence on TLE outcome). Methods: The retrospective analysis of a single centre database containing 3721 TLEs. Results: Unexpected procedure difficulties (UPDs) occurred in 18.43% of cases (singles in 12.20% of cases and multiples in 6.26% of cases). These included blockages in the lead venous approach in3.28% of cases, functional lead dislodgement in 0.91% of cases, and loss of broken lead fragment in 0.60% of cases. All of them, including implant vein—in 7.98% of cases, lead fracture during extraction—in 3.84% of cases, and lead-to-lead adherence—in 6.59% of cases, Byrd dilator collapse—in 3.41% of cases, including the use of an alternative prolonged the procedure but had no influence on long-term mortality. Most of the occurrences were associated with lead dwell time, younger patient age, lead burden, and poorer procedure effectiveness and complications (common cause). However, some of the problems seemed to be related to cardiac implantable electronic devices (CIED) implantation and the subsequent lead management strategy. A more complete list of all tips and tricks is still required. Conclusions: (1) The complexity of the lead extraction procedure combines both prolonged procedure duration and the occurrence of lesser-known UPDs. (2) UPDs are present in nearly one fifth of the TLE procedures, and can occur simultaneously. (3) UPDs, which usually force the extractor to expand the range of techniques and tools, should become part of the training in transvenous lead extraction.