diff --git a/src/server.ts b/src/server.ts
index 16fa63992d08b67809b93144121e314cf0fae9b2..3e68d6f175c0777d7b90a44545206246c3b0fae3 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -435,21 +435,16 @@       try {
         jitModules = {
           generateRules: {
             module: __non_webpack_require__(
-              resolveFrom(configDir, 'tailwindcss/lib/jit/lib/generateRules')
+              resolveFrom(
+                configDir,
+                semver.gte(tailwindcssVersion, '2.1.3')
+                  ? 'tailwindcss/lib/jit/lib/generateRules'
+                  : 'tailwindcss/jit/lib/generateRules'
+              )
             ).generateRules,
           },
         }
-      } catch (_) {
-        try {
-          jitModules = {
-            generateRules: {
-              module: __non_webpack_require__(
-                resolveFrom(configDir, 'tailwindcss/jit/lib/generateRules')
-              ).generateRules,
-            },
-          }
-        } catch (_) {}
-      }
+      } catch (_) {}
     } catch (error) {
       throw new SilentError(error.message)
       // TODO: force mode
@@ -675,17 +670,13 @@     state.plugins = await getPlugins(config)
     state.classNames = (await extractClassNames(postcssResult.root)) as ClassNames
 
     if (state.jit) {
-      let setupContext
-
-      try {
-        setupContext = __non_webpack_require__(
-          resolveFrom(path.dirname(state.configPath), 'tailwindcss/lib/jit/lib/setupContext')
-        ).default
-      } catch (_) {
-        setupContext = __non_webpack_require__(
-          resolveFrom(path.dirname(state.configPath), 'tailwindcss/jit/lib/setupContext')
-        )
-      }
+      let setupContext = semver.gte(tailwindcss.version, '2.1.3')
+        ? __non_webpack_require__(
+            resolveFrom(path.dirname(state.configPath), 'tailwindcss/lib/jit/lib/setupContext')
+          ).default
+        : __non_webpack_require__(
+            resolveFrom(path.dirname(state.configPath), 'tailwindcss/jit/lib/setupContext')
+          )
 
       state.jitContext = setupContext(state.configPath)(
         { opts: {}, messages: [] },