diff --git a/AGENTS.md b/AGENTS.md
index 846537f..6e0211e 100644
--- a/AGENTS.md
+++ b/AGENTS.md
@@ -101,6 +101,7 @@ Each command extends `BaseCommand.cfc` (or `BaseAICommand.cfc` for AI commands)
 - **Always lint markdown files after editing** - Run `npx markdownlint-cli -f {filename}` after any markdown file modifications
 - Markdown linting configuration is in `.markdownlint.json`
 - Fix any linting errors before committing changes
+- **Always update `changelog.md`** for every fix, update, or addition
 
 ## Development Workflows
 
diff --git a/changelog.md b/changelog.md
index 1e0405e..0b1069a 100644
--- a/changelog.md
+++ b/changelog.md
@@ -13,6 +13,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 - `coldbox create handler --boxlang` / `--noboxlang` now propagates language selection to auto-generated views so view extensions match the requested mode (`.bxm` for BoxLang, `.cfm` for CFML)
 - `coldbox create model --tests` now prefixes the right location of the models
+- `coldbox watch-reinit` now honors `server.json` webroot-based server discovery so running apps in subdirectory webroots are correctly found and reinitialized
 
 ## [8.12.0] - 2026-05-11
 
diff --git a/commands/coldbox/watch-reinit.cfc b/commands/coldbox/watch-reinit.cfc
index bdaf851..b21f810 100644
--- a/commands/coldbox/watch-reinit.cfc
+++ b/commands/coldbox/watch-reinit.cfc
@@ -76,7 +76,11 @@ component {
 			"removed" : "red",
 			"changed" : "yellow"
 		}
-		var serverDetails = serverService.resolveServerDetails( {} );
+		var defaultServer = serverService.getServerInfoByDiscovery( serverConfigFile = "server.json" );
+		var serverDetails = serverService.resolveServerDetails( {
+			name      : defaultServer.keyExists( "name" ) ? defaultServer.name : "",
+			directory : getCWD()
+		} );
 		var serverStatus  = serverService.isServerRunning( serverDetails.serverInfo );
 
 		// Tabula rasa