diff --git a/crates/compiler/load_internal/src/file.rs b/crates/compiler/load_internal/src/file.rs
index bd115cd16a..6d4e38495b 100644
--- a/crates/compiler/load_internal/src/file.rs
+++ b/crates/compiler/load_internal/src/file.rs
@@ -3841,8 +3841,7 @@ struct HeaderOutput<'a> {
 fn ensure_roc_file<'a>(filename: &PathBuf, src_bytes: &[u8]) -> Result<(), LoadingProblem<'a>> {
     match filename.extension() {
         Some(ext) => {
-            let roc_ext = std::ffi::OsStr::new("roc");
-            if roc_ext != ext {
+            if ext != ROC_FILE_EXTENSION {
                 return Err(LoadingProblem::FileProblem {
                     filename: filename.clone(),
                     error: io::ErrorKind::Unsupported,
diff --git a/crates/compiler/load_internal/tests/test_load.rs b/crates/compiler/load_internal/tests/test_load.rs
index d5716c1d04..b4a2bce918 100644
--- a/crates/compiler/load_internal/tests/test_load.rs
+++ b/crates/compiler/load_internal/tests/test_load.rs
@@ -1213,10 +1213,10 @@ fn non_roc_file_extension() {
 
     let expected = indoc!(
         r"
-        ── EXPECTED ROC FILE in tmp/non_roc_file_extension/main.md ─────────────────────
+        ── NOT A ROC FILE in tmp/non_roc_file_extension/main.md ────────────────────────
 
-        I am expecting a roc application file with either `.roc` or no
-        extension. Instead I found a file with extension `.md`"
+        I expected a file with extension `.roc` or without extension.
+        Instead I received a file with extension `.md`."
     );
     let color_start = String::from_utf8(vec![27, 91, 51, 54, 109]).unwrap();
     let color_end = String::from_utf8(vec![27, 91, 48, 109]).unwrap();
@@ -1245,13 +1245,15 @@ fn roc_file_no_extension() {
 
     let expected = indoc!(
         r"
-        ── EXPECTED ROC FILE in tmp/roc_file_no_extension/main ─────────────────────────
+        ── NOT A ROC FILE in tmp/roc_file_no_extension/main ────────────────────────────
 
-        I am expecting a roc application file with either `.roc` or no
-        extension and a shebang directive. Instead I found a file without an
-        extension and without a shebang
+        I expected a file with either:
+        - extension `.roc`
+        - no extension and a roc shebang as the first line, e.g.
+        `#!/home/username/bin/roc_nightly/roc`
 
-        Consider starting the file with `#!` and the path to your roc binarya"
+        The provided file did not start with a shebang `#!` containing the
+        string `roc`. Is tmp/roc_file_no_extension/main a Roc file?"
     );
     let color_start = String::from_utf8(vec![27, 91, 51, 54, 109]).unwrap();
     let color_end = String::from_utf8(vec![27, 91, 48, 109]).unwrap();
diff --git a/crates/reporting/src/report.rs b/crates/reporting/src/report.rs
index d3b9a7be9c..b5f242ddf0 100644
--- a/crates/reporting/src/report.rs
+++ b/crates/reporting/src/report.rs
@@ -1654,22 +1654,25 @@ pub fn to_file_problem_report<'b>(
         }
         io::ErrorKind::Unsupported => {
             let doc = match filename.extension() {
-                Some(ext) => {
-                    alloc.concat(vec![
-                        alloc.reflow(
-                            r"I am expecting a roc application file with either `.roc` or no extension. Instead I found a file with extension `.",
-                        ),
-                        alloc.as_string(ext.to_string_lossy()),
-                        alloc.as_string("`"),
-                    ])
-                }
+                Some(ext) => alloc.concat(vec![
+                    alloc.reflow(r"I expected a file with extension `.roc` or without extension."),
+                    alloc.hardline(),
+                    alloc.reflow(r"Instead I received a file with extension `."),
+                    alloc.as_string(ext.to_string_lossy()),
+                    alloc.as_string("`."),
+                ]),
                 None => {
                     alloc.stack(vec![
-                        alloc.concat(vec![
-                            alloc.reflow(r"I am expecting a roc application file with either `.roc` or no extension and a shebang directive. "),
-                            alloc.reflow(r"Instead I found a file without an extension and without a shebang"),
+                        alloc.vcat(vec![
+                            alloc.reflow(r"I expected a file with either:"),
+                            alloc.reflow("- extension `.roc`"),
+                            alloc.reflow("- no extension and a roc shebang as the first line, e.g. `#!/home/username/bin/roc_nightly/roc`"),
                         ]),
-                        alloc.reflow(r"Consider starting the file with `#!` and the path to your roc binary"),
+                        alloc.concat(vec![
+                            alloc.reflow("The provided file did not start with a shebang `#!` containing the string `roc`. Is "),
+                            alloc.as_string(filename.to_string_lossy()),
+                            alloc.reflow(" a Roc file?"),
+                        ])
                     ])
                 }
             };
@@ -1677,7 +1680,7 @@ pub fn to_file_problem_report<'b>(
             Report {
                 filename,
                 doc,
-                title: "EXPECTED ROC FILE".to_string(),
+                title: "NOT A ROC FILE".to_string(),
                 severity: Severity::Fatal,
             }
         }