diff --git a/.gitignore b/.gitignore
index c32621b..fd7ac02 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,3 +1,4 @@
+.DS_Store
 elm-stuff
 node_modules
 dist
diff --git a/cli/src/Main.elm b/cli/src/Main.elm
index 464faa4..bf69e57 100644
--- a/cli/src/Main.elm
+++ b/cli/src/Main.elm
@@ -1,5 +1,6 @@
 module Main exposing (main)
 
+import Path
 import Platform
 import Ports
 
@@ -20,7 +21,7 @@ main =
                 ( ()
                 , case command of
                     "build" ->
-                        Ports.build filepaths
+                        Ports.build (filepaths |> List.map Path.fromFilepath |> List.sortWith Path.routingOrder)
 
                     "add" ->
                         Ports.add { pageType = pageType, name = name }
diff --git a/cli/src/Path.elm b/cli/src/Path.elm
index b7b0f39..b97f517 100644
--- a/cli/src/Path.elm
+++ b/cli/src/Path.elm
@@ -4,6 +4,7 @@ module Path exposing
     , fromModuleName
     , hasParams
     , optionalParams
+    , routingOrder
     , toFilepath
     , toFlags
     , toList
@@ -237,6 +238,44 @@ hasParams path =
     dynamicCount path > 0
 
 
+routingOrder : Path -> Path -> Order
+routingOrder (Internals list1) (Internals list2) =
+    let
+        endsIn : String -> List String -> Bool
+        endsIn str list =
+            list
+                |> List.reverse
+                |> List.head
+                |> (==) (Just str)
+
+        endsInTop =
+            endsIn "Top"
+
+        endsInDynamic =
+            endsIn "Dynamic"
+    in
+    if List.length list1 < List.length list2 then
+        LT
+
+    else if List.length list1 > List.length list2 then
+        GT
+
+    else if endsInTop list1 && not (endsInTop list2) then
+        LT
+
+    else if not (endsInTop list1) && endsInTop list2 then
+        GT
+
+    else if not (endsInDynamic list1) && endsInDynamic list2 then
+        LT
+
+    else if endsInDynamic list1 && not (endsInDynamic list2) then
+        GT
+
+    else
+        EQ
+
+
 
 -- HELPERS
 
diff --git a/cli/src/Ports.elm b/cli/src/Ports.elm
index 6951334..349e0cc 100644
--- a/cli/src/Ports.elm
+++ b/cli/src/Ports.elm
@@ -6,7 +6,7 @@ import Add.Sandbox
 import Add.Static
 import Generators.Pages as Pages
 import Generators.Route as Route
-import Path
+import Path exposing (Path)
 
 
 port addPort : { filepath : String, content : String } -> Cmd msg
@@ -56,17 +56,13 @@ add { name, pageType } =
             uhhh ()
 
 
-build : List String -> Cmd msg
-build filepaths =
-    filepaths
-        |> List.map Path.fromFilepath
-        |> (\paths ->
-                [ { filepath = "Generated/Route.elm"
-                  , content = Route.generate paths
-                  }
-                , { filepath = "Generated/Pages.elm"
-                  , content = Pages.generate paths
-                  }
-                ]
-           )
-        |> buildPort
+build : List Path -> Cmd msg
+build paths =
+    buildPort
+        [ { filepath = "Generated/Route.elm"
+          , content = Route.generate paths
+          }
+        , { filepath = "Generated/Pages.elm"
+          , content = Pages.generate paths
+          }
+        ]
diff --git a/cli/tests/Tests/Path.elm b/cli/tests/Tests/Path.elm
index d498b7e..288de4f 100644
--- a/cli/tests/Tests/Path.elm
+++ b/cli/tests/Tests/Path.elm
@@ -8,7 +8,39 @@ import Test exposing (..)
 suite : Test
 suite =
     describe "Path"
-        [ describe "fromFilepath"
+        [ describe "routingOrder"
+            [ test "prioritizes dynamic last" <|
+                \_ ->
+                    Path.routingOrder
+                        (Path.fromFilepath "Example/Top.elm")
+                        (Path.fromFilepath "Example/Dynamic.elm")
+                        |> Expect.equal LT
+            , test "prioritizes files over folders with top" <|
+                \_ ->
+                    Path.routingOrder
+                        (Path.fromFilepath "Example/Top.elm")
+                        (Path.fromFilepath "Example.elm")
+                        |> Expect.equal GT
+            , test "works with List.sortWith as expected" <|
+                \_ ->
+                    [ Path.fromFilepath "Top.elm"
+                    , Path.fromFilepath "About.elm"
+                    , Path.fromFilepath "Authors/Dynamic/Posts/Dynamic.elm"
+                    , Path.fromFilepath "Posts/Dynamic.elm"
+                    , Path.fromFilepath "Posts.elm"
+                    , Path.fromFilepath "Posts/Top.elm"
+                    ]
+                        |> List.sortWith Path.routingOrder
+                        |> Expect.equalLists
+                            [ Path.fromFilepath "Top.elm"
+                            , Path.fromFilepath "About.elm"
+                            , Path.fromFilepath "Posts.elm"
+                            , Path.fromFilepath "Posts/Top.elm"
+                            , Path.fromFilepath "Posts/Dynamic.elm"
+                            , Path.fromFilepath "Authors/Dynamic/Posts/Dynamic.elm"
+                            ]
+            ]
+        , describe "fromFilepath"
             [ test "ignores first slash" <|
                 \_ ->
                     "/Top.elm"