diff --git a/cli/tests/integration/compile_tests.rs b/cli/tests/integration/compile_tests.rs
index fbe6ffcf57..a6cceb8a7b 100644
--- a/cli/tests/integration/compile_tests.rs
+++ b/cli/tests/integration/compile_tests.rs
@@ -306,8 +306,14 @@ fn compile_with_file_exists_error() {
     .wait_with_output()
     .unwrap();
   assert!(!output.status.success());
-  let expected_stderr =
-    format!("Could not compile: {:?} is a file.\n", &file_path);
+  let expected_stderr = format!(
+    concat!(
+      "Could not compile to file '{}' because its parent directory ",
+      "is an existing file. You can use the `--output <file-path>` flag to ",
+      "provide an alternative name.\n",
+    ),
+    file_path.display(),
+  );
   let stderr = String::from_utf8(output.stderr).unwrap();
   assert!(stderr.contains(&expected_stderr));
 }
@@ -334,8 +340,14 @@ fn compile_with_directory_exists_error() {
     .wait_with_output()
     .unwrap();
   assert!(!output.status.success());
-  let expected_stderr =
-    format!("Could not compile: {:?} is a directory.\n", &exe);
+  let expected_stderr = format!(
+    concat!(
+      "Could not compile to file '{}' because a directory exists with ",
+      "the same name. You can use the `--output <file-path>` flag to ",
+      "provide an alternative name."
+    ),
+    exe.display()
+  );
   let stderr = String::from_utf8(output.stderr).unwrap();
   assert!(stderr.contains(&expected_stderr));
 }
@@ -363,8 +375,14 @@ fn compile_with_conflict_file_exists_error() {
     .wait_with_output()
     .unwrap();
   assert!(!output.status.success());
-  let expected_stderr =
-    format!("Could not compile: cannot overwrite {:?}.\n", &exe);
+  let expected_stderr = format!(
+    concat!(
+      "Could not compile to file '{}' because the file already exists ",
+      "and cannot be overwritten. Please delete the existing file or ",
+      "use the `--output <file-path` flag to provide an alternative name."
+    ),
+    exe.display()
+  );
   let stderr = String::from_utf8(output.stderr).unwrap();
   dbg!(&stderr);
   assert!(stderr.contains(&expected_stderr));
diff --git a/cli/tools/standalone.rs b/cli/tools/standalone.rs
index 8d574aec79..dc9ca45085 100644
--- a/cli/tools/standalone.rs
+++ b/cli/tools/standalone.rs
@@ -183,7 +183,14 @@ pub async fn write_standalone_binary(
   if output.exists() {
     // If the output is a directory, throw error
     if output.is_dir() {
-      bail!("Could not compile: {:?} is a directory.", &output);
+      bail!(
+        concat!(
+          "Could not compile to file '{}' because a directory exists with ",
+          "the same name. You can use the `--output <file-path>` flag to ",
+          "provide an alternative name."
+        ),
+        output.display()
+      );
     }
 
     // Make sure we don't overwrite any file not created by Deno compiler.
@@ -199,7 +206,14 @@ pub async fn write_standalone_binary(
       has_trailer = magic_trailer == MAGIC_TRAILER;
     }
     if !has_trailer {
-      bail!("Could not compile: cannot overwrite {:?}.", &output);
+      bail!(
+        concat!(
+          "Could not compile to file '{}' because the file already exists ",
+          "and cannot be overwritten. Please delete the existing file or ",
+          "use the `--output <file-path` flag to provide an alternative name."
+        ),
+        output.display()
+      );
     }
 
     // Remove file if it was indeed a deno compiled binary, to avoid corruption
@@ -208,7 +222,14 @@ pub async fn write_standalone_binary(
   } else {
     let output_base = &output.parent().unwrap();
     if output_base.exists() && output_base.is_file() {
-      bail!("Could not compile: {:?} is a file.", &output_base);
+      bail!(
+        concat!(
+          "Could not compile to file '{}' because its parent directory ",
+          "is an existing file. You can use the `--output <file-path>` flag to ",
+          "provide an alternative name.",
+        ),
+        output_base.display(),
+      );
     }
     tokio::fs::create_dir_all(output_base).await?;
   }