Peripherally Inserted Central Catheters and Midline Catheters are particularly attractive because of their favorable risk/benefit ratio. If the ideal venipuncture site is in an area inappropriate for catheter emergence, a valid alternative is the tunneling technique, which allows the exit site to be moved to reach the optimal position. There are two main types of tunneling techniques: standard tunnel, using a tunneling device (metal tunneler or peel-away tunneler), and pseudo-tunnel. As much as both are recognized as appropriate and safe, there are still few literature data indicating the criteria for choosing and using the two techniques and the possible related complications. This retrospective observational investigation analyzed data regarding intra- and post-procedural complications of tunneled catheters inserted using two different techniques. The sample was stratified into three subgroups: (1) Standard Tunnel (patients with no PLT or INR disorders), (2) Pseudotunnel (patients with no PLT or INR disorders), and (3) Pseudotunnel (patients with any PLT or INR disorder). Data regarding the procedure, at 24 h and 7 days were collected and analyzed. A total of 143 patients who underwent tunneled catheter insertion were included in the study. Among these, 113 patients were divided into subgroups 1 and 2 and 30 were assigned to subgroup 3. No significant differences were found among the three subgroups regarding immediate, short, and medium-term tunnel complications. The findings of this study suggest that both standard and pseudo-tunnels provide comparable levels of safety and comfort for patients. It was noted that Pseudotunnel offers an equivalent level of safety for patients with coagulation disorders related to PLT and INR, rendering it comparable to a "minimally invasive procedure," which necessitates the same precautions as a non-tunneled PICC.