diff --git a/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicIfDirective.expected.test b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicIfDirective.expected.test
new file mode 100644
index 000000000..e5f573d6d
--- /dev/null
+++ b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicIfDirective.expected.test
@@ -0,0 +1,5 @@
+using System;
+
+#if DEBUG
+using Insite.Bad;
+#endif
diff --git a/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicIfDirective.test b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicIfDirective.test
new file mode 100644
index 000000000..df5f9a193
--- /dev/null
+++ b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicIfDirective.test
@@ -0,0 +1,4 @@
+#if DEBUG
+using Insite.Bad;
+#endif
+using System;
\ No newline at end of file
diff --git a/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicSort.expected.test b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicSort.expected.test
new file mode 100644
index 000000000..42caaf782
--- /dev/null
+++ b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicSort.expected.test
@@ -0,0 +1,5 @@
+using AWord;
+using BWord;
+using MWord;
+using YWord;
+using ZWord;
diff --git a/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicSort.test b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicSort.test
new file mode 100644
index 000000000..0e3e608c7
--- /dev/null
+++ b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_BasicSort.test
@@ -0,0 +1,5 @@
+using MWord;
+using ZWord;
+using AWord;
+using BWord;
+using YWord;
\ No newline at end of file
diff --git a/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_SortsSystemToTop.expected.test b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_SortsSystemToTop.expected.test
new file mode 100644
index 000000000..f2122728b
--- /dev/null
+++ b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_SortsSystemToTop.expected.test
@@ -0,0 +1,6 @@
+using System;
+
+using System.Web; // keeping the space above this is odd, but there isn't a good way to know which spaces to remove besides the first one
+
+using AWord;
+using ZWord;
diff --git a/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_SortsSystemToTop.test b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_SortsSystemToTop.test
new file mode 100644
index 000000000..f5c6fa852
--- /dev/null
+++ b/Src/CSharpier.Tests/FormattingTests/TestFiles/cs/UsingDirectives_SortsSystemToTop.test
@@ -0,0 +1,6 @@
+using ZWord;
+
+using AWord; // the blank line above here tests that we don't add two blank lines between system and non-system
+
+using System.Web; // keeping the blank line above this in the expected is odd, but there isn't a good way to know which spaces to remove besides the first one
+using System;
diff --git a/Src/CSharpier/SyntaxPrinter/NamespaceLikePrinter.cs b/Src/CSharpier/SyntaxPrinter/NamespaceLikePrinter.cs
index aeb783a5e..043bf5969 100644
--- a/Src/CSharpier/SyntaxPrinter/NamespaceLikePrinter.cs
+++ b/Src/CSharpier/SyntaxPrinter/NamespaceLikePrinter.cs
@@ -44,19 +44,7 @@ FormattingContext context
                 docs.Add(Doc.HardLine);
             }
 
-            docs.Add(
-                Doc.Join(
-                    Doc.HardLine,
-                    usings.Select(
-                        (o, i) =>
-                            UsingDirective.Print(
-                                o,
-                                context,
-                                printExtraLines: i != 0 || externs.Count != 0
-                            )
-                    )
-                )
-            );
+            docs.Add(UsingDirectives.PrintWithSorting(usings, context, externs.Count != 0));
         }
 
         var isCompilationUnitWithAttributes = false;
diff --git a/Src/CSharpier/SyntaxPrinter/UsingDirectives.cs b/Src/CSharpier/SyntaxPrinter/UsingDirectives.cs
new file mode 100644
index 000000000..2f3918b4e
--- /dev/null
+++ b/Src/CSharpier/SyntaxPrinter/UsingDirectives.cs
@@ -0,0 +1,104 @@
+namespace CSharpier.SyntaxPrinter;
+
+internal static class UsingDirectives
+{
+    private static readonly DefaultOrder Comparer = new();
+
+    // TODO what does the analyzer do with some of these sorts?
+    // TODO what about validation?
+    // TODO what about #ifs?
+    // TODO what about globals?
+    // TODO what about statics?
+    // TODO what about alias?
+    // TODO get rid of lines and keep them in blocks? - this does https://google.github.io/styleguide/javaguide.html#s3.3-import-statements
+    // TODO what about alias any type with c# 12?
+
+    public static Doc PrintWithSorting(
+        SyntaxList<UsingDirectiveSyntax> usings,
+        FormattingContext context,
+        bool printExtraLines
+    )
+    {
+        var sortedUsings = usings.OrderBy(o => o, Comparer).ToArray();
+        var docs = new List<Doc>();
+
+        var lastWasSystem = false;
+        for (var i = 0; i < sortedUsings.Length; i++)
+        {
+            var noExtraLines = false;
+            var thisIsSystem = sortedUsings[i].Name is NameSyntax name && IsSystemName(name);
+            if (i != 0)
+            {
+                docs.Add(Doc.HardLine);
+                if (!thisIsSystem && lastWasSystem)
+                {
+                    noExtraLines = true;
+                    docs.Add(Doc.HardLine);
+                }
+
+                lastWasSystem = thisIsSystem;
+            }
+            docs.Add(
+                UsingDirective.Print(
+                    sortedUsings[i],
+                    context,
+                    printExtraLines: (i != 0 || printExtraLines) && !noExtraLines
+                )
+            );
+        }
+
+        return Doc.Concat(docs);
+    }
+
+    private static bool IsSystemName(NameSyntax value)
+    {
+        while (true)
+        {
+            if (value is not QualifiedNameSyntax qualifiedNameSyntax)
+            {
+                return value is IdentifierNameSyntax { Identifier.Text: "System" };
+            }
+            value = qualifiedNameSyntax.Left;
+        }
+    }
+
+    private class DefaultOrder : IComparer<UsingDirectiveSyntax>
+    {
+        public int Compare(UsingDirectiveSyntax? x, UsingDirectiveSyntax? y)
+        {
+            if (x?.Name is null)
+            {
+                return -1;
+            }
+
+            if (y?.Name is null)
+            {
+                return 1;
+            }
+
+            var xIsSystem = IsSystemName(x.Name);
+            var yIsSystem = IsSystemName(y.Name);
+
+            int Return(int value)
+            {
+                DebugLogger.Log(
+                    $"{x.ToFullString().Trim()} {xIsSystem} vs {y.ToFullString().Trim()} {yIsSystem} = {value}"
+                );
+
+                return value;
+            }
+
+            if (xIsSystem && !yIsSystem)
+            {
+                return Return(-1);
+            }
+
+            if (!xIsSystem && yIsSystem)
+            {
+                return Return(1);
+            }
+
+            return Return(x.Name.ToFullString().CompareTo(y.Name.ToFullString()));
+        }
+    }
+}