diff --git a/src/jit/lib/setupContextUtils.js b/src/jit/lib/setupContextUtils.js
index 1b35fa405..2506d37ad 100644
--- a/src/jit/lib/setupContextUtils.js
+++ b/src/jit/lib/setupContextUtils.js
@@ -478,8 +478,9 @@ export function getContext(
   getTailwindConfig
 ) {
   let sourcePath = result.opts.from
-  let [tailwindConfig, userConfigPath, tailwindConfigHash, configDependencies] =
-    getTailwindConfig(configOrPath)
+  let [tailwindConfig, userConfigPath, tailwindConfigHash, configDependencies] = getTailwindConfig(
+    configOrPath
+  )
   let isConfigFile = userConfigPath !== null
 
   let contextDependencies = new Set(configDependencies)
@@ -581,6 +582,11 @@ export function getContext(
     stylesheetCache: null, // Hit
   }
 
+  if (!existingContext) {
+    // If we didn't have an existing modified map then populate it now.
+    trackModified([...contextDependencies], context)
+  }
+
   // ---
 
   // Update all context tracking state