If I update my server to craftbukkit to 1.5.2 will it affect these plugins I have on the server? [PluginList] Citizens version 2.0.8-SNAPSHOT (build 792) QuickShop version 4.0 GroupManager version 2.0 (Dev2.9.640) (Phoenix) Portals version 1.2.4 Transporter version 8.14 WorldEdit version 5.5.5 mcjobs version 3.1.8 ColoredSigns version 1.2 SpamGuard version 1.1 War version 1.7.4 (Doolittle) Multiverse-Core version 2.4-b527 WorldGuard version 5.7.3 HeadHunter version 1.3.4 AutoCast version 1.3.1 Chairs version 2.0.2 iConomy version 7.0 WarpSigns version 2.0 AntiXRay version 1.6.0 Lockette version 1.7.9 Votifier version 1.9 SuperSpleef version B 0.1.5 MonsterBox version 0.9.0 MobArena version 0.94.4.96 Essentials version 2.10.1 EssentialsProtect version 2.10.1 EssentialsSpawn version 2.10.1 Multiverse-Inventories version 2.5-b335 Enjin Minecraft Plugin version 2.4.2 EssentialsAntiBuild version 2.10.1 ChestShop version 3.46 EssentialsChat version 2.10.1 Factions version 1.6.9.4
Download a copy of all of your plugins to a test server, update the test server, and see if any stop working?
First update your plugins, chest shop is outdated, multiverse too, worldguard and worldedit too and maybe some others
Loads of plugins will break when updating. Citizens, WorldGuard, WorldEdit, probably Essentials, probably Factions, and probably some others too. Better make a test server and see what plugins cause issues when starting.