diff --git a/src/config.ts b/src/config.ts
index 9c3db9e..b97abc8 100644
--- a/src/config.ts
+++ b/src/config.ts
@@ -123,12 +123,18 @@ async function loadTailwindConfig(
     let pkgFile = resolveJsFrom(baseDir, `${pkgName}/package.json`)
     let pkgDir = path.dirname(pkgFile)
 
+    // If the user doesn't define an entrypoint then we use the default theme
+    entryPoint = entryPoint ?? `${pkgDir}/theme.css`
+
     try {
-      let v4 = await loadV4(baseDir, pkgDir, pkgName, entryPoint)
-      if (v4) {
-        return v4
-      }
-    } catch {}
+      let v4 = await loadV4(baseDir, pkgName, entryPoint)
+      if (v4) return v4
+    } catch (err) {
+      console.error(
+        `Unable to load your Tailwind CSS v4 stylesheet: ${entryPoint}`,
+      )
+      console.error(err)
+    }
 
     resolveConfig = require(path.join(pkgDir, 'resolveConfig'))
     createContext = require(
@@ -142,10 +148,18 @@ async function loadTailwindConfig(
     loadConfig = require(path.join(pkgDir, 'loadConfig'))
   } catch {}
 
-  if (tailwindConfigPath) {
-    clearModule(tailwindConfigPath)
-    const loadedConfig = loadConfig(tailwindConfigPath)
-    tailwindConfig = loadedConfig.default ?? loadedConfig
+  try {
+    if (tailwindConfigPath) {
+      clearModule(tailwindConfigPath)
+      const loadedConfig = loadConfig(tailwindConfigPath)
+      tailwindConfig = loadedConfig.default ?? loadedConfig
+    }
+  } catch (err) {
+    console.error(
+      `Unable to load your Tailwind CSS v3 config: ${tailwindConfigPath}`,
+    )
+
+    throw err
   }
 
   // suppress "empty content" warning
@@ -204,24 +218,14 @@ function createLoader<T>({
   }
 }
 
-async function loadV4(
-  baseDir: string,
-  pkgDir: string,
-  pkgName: string,
-  entryPoint: string | null,
-) {
+async function loadV4(baseDir: string, pkgName: string, entryPoint: string) {
   // Import Tailwind — if this is v4 it'll have APIs we can use directly
   let pkgPath = resolveJsFrom(baseDir, pkgName)
 
   let tw = await import(pathToFileURL(pkgPath).toString())
 
   // This is not Tailwind v4
-  if (!tw.__unstable__loadDesignSystem) {
-    return null
-  }
-
-  // If the user doesn't define an entrypoint then we use the default theme
-  entryPoint = entryPoint ?? `${pkgDir}/theme.css`
+  if (!tw.__unstable__loadDesignSystem) return null
 
   // Create a Jiti instance that can be used to load plugins and config files
   let jiti = createJiti(import.meta.url, {
@@ -232,7 +236,9 @@ async function loadV4(
   let importBasePath = path.dirname(entryPoint)
 
   // Resolve imports in the entrypoint to a flat CSS tree
-  let css = await fs.readFile(entryPoint, 'utf-8')
+  let css: string
+
+  css = await fs.readFile(entryPoint, 'utf-8')
 
   // Determine if the v4 API supports resolving `@import`
   let supportsImports = false
@@ -354,12 +360,38 @@ function getConfigPath(options: ParserOptions, baseDir: string): string | null {
 
 function getEntryPoint(options: ParserOptions, baseDir: string): string | null {
   if (options.tailwindStylesheet) {
+    if (
+      options.tailwindStylesheet.endsWith('.js') ||
+      options.tailwindStylesheet.endsWith('.mjs') ||
+      options.tailwindStylesheet.endsWith('.cjs') ||
+      options.tailwindStylesheet.endsWith('.ts') ||
+      options.tailwindStylesheet.endsWith('.mts') ||
+      options.tailwindStylesheet.endsWith('.cts')
+    ) {
+      console.error(
+        "Your `tailwindStylesheet` option points to a JS/TS config file. You must point to your project's `.css` file for v4 projects.",
+      )
+    } else if (
+      options.tailwindStylesheet.endsWith('.sass') ||
+      options.tailwindStylesheet.endsWith('.scss') ||
+      options.tailwindStylesheet.endsWith('.less') ||
+      options.tailwindStylesheet.endsWith('.styl')
+    ) {
+      console.error(
+        'Your `tailwindStylesheet` option points to a preprocessor file. This is unsupported and you may get unexpected results.',
+      )
+    } else if (!options.tailwindStylesheet.endsWith('.css')) {
+      console.error(
+        'Your `tailwindStylesheet` option does not point to a CSS file. This is unsupported and you may get unexpected results.',
+      )
+    }
+
     return path.resolve(baseDir, options.tailwindStylesheet)
   }
 
   if (options.tailwindEntryPoint) {
     console.warn(
-      'Use the `tailwindStylesheet` option for v4 projects instead of `tailwindEntryPoint`.',
+      'Deprecated: Use the `tailwindStylesheet` option for v4 projects instead of `tailwindEntryPoint`.',
     )
 
     return path.resolve(baseDir, options.tailwindEntryPoint)
@@ -367,7 +399,7 @@ function getEntryPoint(options: ParserOptions, baseDir: string): string | null {
 
   if (options.tailwindConfig && options.tailwindConfig.endsWith('.css')) {
     console.warn(
-      'Use the `tailwindStylesheet` option for v4 projects instead of `tailwindConfig`.',
+      'Deprecated: Use the `tailwindStylesheet` option for v4 projects instead of `tailwindConfig`.',
     )
 
     return path.resolve(baseDir, options.tailwindConfig)