diff --git a/wpimath/generate_numbers.py b/wpimath/generate_numbers.py
index 61cc02a7ed..701f3e652b 100644
--- a/wpimath/generate_numbers.py
+++ b/wpimath/generate_numbers.py
@@ -1,42 +1,59 @@
 import os
-import shutil
 import sys
 
-MAX_NUM = 20
 
-dirname, _ = os.path.split(os.path.abspath(__file__))
-cmake_binary_dir = sys.argv[1]
+def main():
+    MAX_NUM = 20
 
-with open(f"{dirname}/src/generate/GenericNumber.java.in", "r") as templateFile:
-    template = templateFile.read()
-    rootPath = f"{cmake_binary_dir}/generated/main/java/edu/wpi/first/wpiutil/math/numbers"
+    dirname, _ = os.path.split(os.path.abspath(__file__))
+    cmake_binary_dir = sys.argv[1]
 
-    if os.path.exists(rootPath):
-        shutil.rmtree(rootPath)
-    os.makedirs(rootPath)
+    with open(f"{dirname}/src/generate/GenericNumber.java.in",
+              "r") as templateFile:
+        template = templateFile.read()
+        rootPath = f"{cmake_binary_dir}/generated/main/java/edu/wpi/first/wpiutil/math/numbers"
 
-    for i in range(MAX_NUM + 1):
-        with open(f"{rootPath}/N{i}.java", "w") as f:
-            f.write(template.replace("${num}", str(i)))
+        if not os.path.exists(rootPath):
+            os.makedirs(rootPath)
 
-with open(f"{dirname}/src/generate/Nat.java.in", "r") as templateFile:
-    template = templateFile.read()
-    outputPath = f"{cmake_binary_dir}/generated/main/java/edu/wpi/first/wpiutil/math/Nat.java"
-    with open(f"{dirname}/src/generate/NatGetter.java.in", "r") as getterFile:
-        getter = getterFile.read()
+        for i in range(MAX_NUM + 1):
+            new_contents = template.replace("${num}", str(i))
 
-    if os.path.exists(outputPath):
-        os.remove(outputPath)
+            if os.path.exists(f"{rootPath}/N{i}.java"):
+                with open(f"{rootPath}/N{i}.java", "r") as f:
+                    if f.read() == new_contents:
+                        continue
 
-    importsString = ""
+            # File either doesn't exist or has different contents
+            with open(f"{rootPath}/N{i}.java", "w") as f:
+                f.write(new_contents)
 
-    for i in range(MAX_NUM + 1):
-        importsString += f"import edu.wpi.first.wpiutil.math.numbers.N{i};\n"
-        template += getter.replace("${num}", str(i))
+    with open(f"{dirname}/src/generate/Nat.java.in", "r") as templateFile:
+        template = templateFile.read()
+        outputPath = f"{cmake_binary_dir}/generated/main/java/edu/wpi/first/wpiutil/math/Nat.java"
+        with open(f"{dirname}/src/generate/NatGetter.java.in",
+                  "r") as getterFile:
+            getter = getterFile.read()
 
-    template += "}\n"
+        importsString = ""
 
-    template = template.replace('{{REPLACEWITHIMPORTS}}', importsString)
+        for i in range(MAX_NUM + 1):
+            importsString += f"import edu.wpi.first.wpiutil.math.numbers.N{i};\n"
+            template += getter.replace("${num}", str(i))
 
-    with open(outputPath, "w") as f:
-        f.write(template)
+        template += "}\n"
+
+        template = template.replace('{{REPLACEWITHIMPORTS}}', importsString)
+
+        if os.path.exists(outputPath):
+            with open(outputPath, "r") as f:
+                if f.read() == template:
+                    return 0
+
+        # File either doesn't exist or has different contents
+        with open(outputPath, "w") as f:
+            f.write(template)
+
+
+if __name__ == "__main__":
+    main()