diff --git a/src/main/wacc/Main.scala b/src/main/wacc/Main.scala
index 750a548..c85e2db 100644
--- a/src/main/wacc/Main.scala
+++ b/src/main/wacc/Main.scala
@@ -18,20 +18,35 @@ import org.typelevel.log4cats.slf4j.Slf4jLogger
 import org.typelevel.log4cats.Logger
 
 import assemblyIR as asm
+import java.nio.file.Paths
 
-// TODO: IO correctness, --greedy, parallelisable, and probably splitting this file up
+/*
+TODO:
+  1) IO correctness
+  2)  --greedy,
+  3) parallelised compilation
+  4) splitting the file up and nicer refactoring
+  5) logging could be removed
+  6) errors can be handled more gracefully probably
+ */
 
 given Argument[Path] = Argument.from("path") { str =>
-  val path = Path.of(str)
-  (
-    Either.cond(Files.exists(path), path, s"File '${path.toAbsolutePath}' does not exist"),
-    Either.cond(
-      Files.isRegularFile(path),
-      path,
-      s"File '${path.toAbsolutePath}' must be a regular file"
-    ),
-    Either.cond(path.toString.endsWith(".wacc"), path, "File must have .wacc extension")
-  ).mapN((_, _, _) => path).toValidatedNel
+  val path =
+    if (str.startsWith("~")) Paths.get(System.getProperty("user.home"), str.drop(1)) // Expand ~
+    else Paths.get(str).toAbsolutePath.normalize() // TODO: normalize or not?
+
+  if (path.toString.endsWith(".wacc")) {
+    (
+      Either.cond(Files.exists(path), path, s"File '${path.toAbsolutePath}' does not exist"),
+      Either.cond(
+        Files.isRegularFile(path),
+        path,
+        s"File '${path.toAbsolutePath}' must be a regular file"
+      )
+    ).mapN((_, _) => path).toValidatedNel
+  } else {
+    Right(path).toValidatedNel
+  }
 }
 
 given logger: Logger[IO] = Slf4jLogger.getLogger[IO]
@@ -93,6 +108,15 @@ def compile(filePath: Path, outputDir: Option[Path], log: Boolean): IO[Int] = {
     IO.blocking {
       Files.createDirectories(outDir)
       outDir
+    }.handleErrorWith {
+      // TODO: I think this wont occur if a user runs with privileges but this must be checked
+      // TODO: this will return the ugly stack trace, one could refactor compileCommand to
+      case _: java.nio.file.AccessDeniedException =>
+        IO.raiseError(
+          new Exception(
+            s"Permission denied: Cannot create directory '${outDir.toAbsolutePath}'. Try choosing a different output path or run as root."
+          )
+        )
     }
 
   // TODO: path, file , the names are confusing (when Path is the type but we are working with files)
@@ -123,7 +147,12 @@ val compileCommand: Opts[IO[ExitCode]] =
   (filesOpt, logOpt, outputOpt).mapN { (files, log, outDir) =>
     files
       .traverse { file =>
-        compile(file.toAbsolutePath, outDir, log)
+        compile(file.toAbsolutePath, outDir, log).handleErrorWith { err =>
+          // TODO: probably a more elegant way of doing this
+          // also, -1 arbitrary
+          // also - this outputs two messages for some reason
+          logger.error(err.getMessage) // *> IO.pure(ExitCode(-1))
+        }
       }
       .map { exitCodes =>
         if (exitCodes.exists(_ != 0))