diff --git a/compare50/__main__.py b/compare50/__main__.py
index bc6212f..ad98b36 100644
--- a/compare50/__main__.py
+++ b/compare50/__main__.py
@@ -19,6 +19,7 @@
 import attr
 import lib50
 import termcolor
+import pygments
 
 from . import comparators, _api, _data, _renderer, __version__
 
@@ -245,6 +246,26 @@ def get_non_empty_subs(subs):
     def get_undecodable_files(subs):
         return [sub.path / file for sub in subs for file in sub.undecodable_files]
 
+    def warn_txt_files(subs):
+        """Warn about plaintext or code in file when the user submits a .txt file"""
+        for sub in subs:
+            for file in sub.files:
+                if file.name.suffix == ".txt":
+                    try:
+                        lexer = pygments.lexers.guess_lexer(file.read())
+                    except pygments.util.ClassNotFound:
+                        lexer = pygments.lexers.special.TextLexer()
+
+                    # If the file is interpreted as a plaintext file
+                    if isinstance(lexer, pygments.lexers.special.TextLexer):
+                        termcolor.cprint(
+                        f"{file.name.name} appears to be plaintext. Scoring using `structure` could produce unexpected results.",
+                        "yellow", attrs=["bold"])
+                    else:
+                        termcolor.cprint(
+                        f"{file.name.name} is a .txt file that appears to contain code. Interpreting as: {lexer.name}",
+                        "yellow", attrs=["bold"])
+
     # Print the number of subs, archives, distro files, and the average number of files per sub
     n_subs = len(get_non_empty_subs(subs))
     n_archives = len(get_non_empty_subs(archives))
@@ -285,6 +306,11 @@ def get_undecodable_files(subs):
         print_warning(undecodable, undecodable_archive, undecodable_distro, "non utf-8")
         did_print_warning = True
 
+    # Warn about txt files
+    warn_txt_files(subs)
+    warn_txt_files(archives)
+    warn_txt_files(distro_subs)
+
     # Print suggestion to run with --verbose if any files are excluded
     if not verbose and did_print_warning:
         termcolor.cprint("Rerun with --verbose to see which files are excluded",
diff --git a/compare50/_data.py b/compare50/_data.py
index c9b17d7..c1b76f4 100644
--- a/compare50/_data.py
+++ b/compare50/_data.py
@@ -183,7 +183,19 @@ def tokens(self):
 
     def lexer(self):
         """Determine which Pygments lexer should be used."""
+        def read_and_guess_lexer():
+            """Reads a file, guesses an appropriate lexer. Fallback to plaintext."""
+            try:
+                return pygments.lexers.guess_lexer(self.read())
+            except pygments.util.ClassNotFound:
+                return pygments.lexers.special.TextLexer()
+
         ext = self.name.suffix
+
+        # if this is a txt file, assume its some kind of code and infer its lexer
+        if ext == '.txt':
+            return read_and_guess_lexer()
+
         try:
             return self._lexer_cache[ext]
         except KeyError:
@@ -195,10 +207,7 @@ def lexer(self):
             self._lexer_cache[ext] = lexer
             return lexer
         except pygments.util.ClassNotFound:
-            try:
-                return pygments.lexers.guess_lexer(self.read())
-            except pygments.util.ClassNotFound:
-                return pygments.lexers.special.TextLexer()
+            return read_and_guess_lexer()
 
     @classmethod
     def get(cls, id):
@@ -207,7 +216,7 @@ def get(cls, id):
 
     def unprocessed_tokens(self):
         """Get the raw tokens of the file."""
-        text = self.read()
+        text  = self.read()
         lexer_tokens = self.lexer().get_tokens_unprocessed(text)
         tokens = []
         prevToken = None