This study analyzed the optimal biliary stenting strategy for palliation in cholangiocarcinoma (CCA). This was a retrospective study of patients with CCA who underwent biliary drainage from 1997 to 2023. A per-patient analysis of percutaneous transhepatic biliary drainage (PTBD) rates, the median number of ERCPs, and overall survival (OS) and a per-procedure analysis of clinical success (CS), stent-specific adverse events (AEs), and mean time to repeat ERCP by stent type and laterality (unilateral and bilateral) are presented. A total of 333 patients underwent 1050 ERCPs, 85% with plastic stents (PSs). PTBD was eventually done in 23% of PS patients, 35% of whom had their PS removed before PTBD. ERCPs with the use of self-expandable metal stents (SEMSs)/unilateral SEMSs had higher CS (89%/91%) versus PSs/unilateral plastic stents (uPSs) (85% both) and PSs within SEMSs (PS-SEMSs)/uPS-SEMSs (71%/74%; P= .013/P= .054). Compared with PSs, SEMSs and PS-SEMSs were associated with higher stent-specific AEs (odds ratios [ORs]: SEMSs 4.85 [95% confidence interval (CI), 3.23-7.27], PS-SEMSs 9.99 [95% CI, 5.33-18.71]; P< .001). Straight PSs were associated with more stent-specific AEs compared with double-pigtail stents (OR 6.74 [95% CI, 3.95-11.45]; P< .001). More 7F stents were used in cases with balloon dilation (BD) (109 with BD vs 88 without BD; P< .001). BD had a 79% CS rate versus 87% without BD (P< .001). Cases with pus on ERCP and those with BD had a shorter mean time to repeat ERCP. On regression analyses, higher Bismuth class, PS use, and PS-SEMS use were associated with a shorter mean time to repeat ERCP. Fifty-two percent of patients in the bilateral SEMS arm died from cholangitis (P= .005). The relatively higher CS rate of SEMSs is countered by the higher stent-specific AE rate. PSs can be removed and may better facilitate PTBD. Within PS types, double-pigtail stents may have fewer stent-specific AEs. Cases requiring BD and with endoscopic evidence of pus may benefit from earlier reintervention.