Update file error messages

2 files changed, 28 insertions, 10 deletions

diff --git a/bot/exts/utils/snekbox/_cog.py b/bot/exts/utils/snekbox/_cog.py
index 605f0fa15..a46fb8f44 100644
--- a/bot/exts/utils/snekbox/_cog.py
+++ b/bot/exts/utils/snekbox/_cog.py
@@ -350,12 +350,26 @@ class Snekbox(Cog):
 
             # Filter file extensions
             allowed, blocked = self._filter_files(ctx, result.files)
+            # Also scan failed files for blocked extensions
+            failed_files = [FileAttachment(name, b"") for name in result.failed_files]
+            blocked.extend(self._filter_files(ctx, failed_files).blocked)
             # Add notice if any files were blocked
             if blocked:
-                msg += (
-                    f"\n{Emojis.failmail} Some files with disallowed extensions can't be uploaded: "
-                    f"**{', '.join(f.suffix for f in blocked)}**"
-                )
+                blocked_sorted = sorted(set(f.suffix for f in blocked))
+                # Only no extension
+                if len(blocked_sorted) == 1 and blocked_sorted[0] == "":
+                    blocked_msg = "Files with no extension can't be uploaded."
+                # Both
+                elif "" in blocked_sorted:
+                    blocked_str = ", ".join(ext for ext in blocked_sorted if ext)
+                    blocked_msg = (
+                        f"Files with no extension or disallowed extensions can't be uploaded: **{blocked_str}**"
+                    )
+                else:
+                    blocked_str = ", ".join(blocked_sorted)
+                    blocked_msg = f"Files with disallowed extensions can't be uploaded: **{blocked_str}**"
+
+                msg += f"\n{Emojis.failmail} {blocked_msg}"
 
             filter_cog: Filtering | None = self.bot.get_cog("Filtering")
             if filter_cog and (await filter_cog.filter_snekbox_output(msg, ctx.message)):
diff --git a/bot/exts/utils/snekbox/_eval.py b/bot/exts/utils/snekbox/_eval.py
index b88225adc..93262959a 100644
--- a/bot/exts/utils/snekbox/_eval.py
+++ b/bot/exts/utils/snekbox/_eval.py
@@ -66,7 +66,7 @@ class EvalResult:
     def status_emoji(self) -> str:
         """Return an emoji corresponding to the status code or lack of output in result."""
         # If there are attachments, skip empty output warning
-        if not self.stdout.strip() and not self.files:  # No output
+        if not self.stdout.strip() and not (self.files or self.failed_files):
             return ":warning:"
         elif self.returncode == 0:  # No error
             return ":white_check_mark:"
@@ -92,14 +92,18 @@ class EvalResult:
         failed_files = f"({self.get_failed_files_str()})"
 
         n_failed = len(self.failed_files)
-        files = f"file{'s' if n_failed > 1 else ''}"
-        msg = f"{Emojis.failmail} Failed to upload {n_failed} {files} {failed_files}"
+        s_upload = "uploads" if n_failed > 1 else "upload"
 
+        msg = f"{Emojis.failmail} {n_failed} file {s_upload} {failed_files} failed"
+
+        # Exceeded file count limit
         if (n_failed + len(self.files)) > FILE_COUNT_LIMIT:
-            it_they = "they" if n_failed > 1 else "it"
-            msg += f" as {it_they} exceeded the {FILE_COUNT_LIMIT} file limit."
+            s_it = "they" if n_failed > 1 else "it"
+            msg += f" as {s_it} exceeded the {FILE_COUNT_LIMIT} file limit."
+        # Exceeded file size limit
         else:
-            msg += f". File sizes should each not exceed {sizeof_fmt(FILE_SIZE_LIMIT)}."
+            s_each_file = "each file's" if n_failed > 1 else "its file"
+            msg += f" because {s_each_file} size exceeds {sizeof_fmt(FILE_SIZE_LIMIT)}."
 
         return msg