diff --git a/tests/Spec/Nri/Ui/Highlighter.elm b/tests/Spec/Nri/Ui/Highlighter.elm
index 5a5f5cc2..752bb9b9 100644
--- a/tests/Spec/Nri/Ui/Highlighter.elm
+++ b/tests/Spec/Nri/Ui/Highlighter.elm
@@ -27,7 +27,6 @@ spec =
         , describe "markdown highlightable behavior" markdownContentTests
         , describe "markdown highlight name behavior" markdownHighlightNameTests
         , describe "joinAdjacentInteractiveHighlights" joinAdjacentInteractiveHighlightsTests
-        , describe "selectShortest" selectShortestTests
         , describe "overlapping highlights" overlappingHighlightTests
         ]
 
@@ -727,116 +726,6 @@ joinAdjacentInteractiveHighlightsTests =
     ]
 
 
-selectShortestTests : List Test
-selectShortestTests =
-    let
-        init highlightables =
-            Highlighter.init
-                { id = "test-highlighter-container"
-                , highlightables = highlightables
-                , marker = markerModel (Just "A")
-                , joinAdjacentInteractiveHighlights = False
-                , sorter = Sort.alphabetical
-                }
-    in
-    [ test "without any highlightables, returns Nothing" <|
-        \() ->
-            init []
-                |> Highlighter.selectShortest (.highlightables >> List.Extra.getAt 0)
-                |> Expect.equal Nothing
-    , test "with 1 unmarked highlightable, returns Nothing" <|
-        \() ->
-            init [ Highlightable.initInteractive [] 0 "hello" ]
-                |> Highlighter.selectShortest (.highlightables >> List.Extra.getAt 0)
-                |> Expect.equal Nothing
-    , test "with 1 marked highlightable, returns the singular mark type" <|
-        \() ->
-            init [ Highlightable.initInteractive [ marker (Just "B") ] 0 "hello" ]
-                |> Highlighter.selectShortest (.highlightables >> List.Extra.getAt 0)
-                |> Expect.equal (Just "B")
-    , test "with 1 multi-marked highlightable, returns one of the mark types depending on sort order" <|
-        \() ->
-            init
-                [ Highlightable.initInteractive
-                    [ marker (Just "C")
-                    , marker (Just "B")
-                    , marker (Just "D")
-                    ]
-                    0
-                    "hello"
-                ]
-                |> Highlighter.selectShortest (.highlightables >> List.Extra.getAt 0)
-                |> Expect.equal (Just "B")
-    , test "with multiple marked highlightables, selecting the first highlightable, returns the shortest mark type" <|
-        \() ->
-            init
-                [ Highlightable.initInteractive
-                    [ marker (Just "C")
-                    , marker (Just "B")
-                    ]
-                    0
-                    "hello"
-                , Highlightable.initInteractive
-                    [ marker (Just "B")
-                    ]
-                    1
-                    "world"
-                , Highlightable.initInteractive
-                    [ marker (Just "C")
-                    ]
-                    2
-                    "!"
-                ]
-                |> Highlighter.selectShortest (.highlightables >> List.Extra.getAt 0)
-                |> Expect.equal (Just "C")
-    , test "with multiple marked highlightables, selecting the second highlightable, returns the shortest mark type" <|
-        \() ->
-            init
-                [ Highlightable.initInteractive
-                    [ marker (Just "B")
-                    ]
-                    0
-                    "hello"
-                , Highlightable.initInteractive
-                    [ marker (Just "B")
-                    , marker (Just "C")
-                    ]
-                    1
-                    "world"
-                , Highlightable.initInteractive
-                    [ marker (Just "C")
-                    ]
-                    2
-                    "!"
-                ]
-                |> Highlighter.selectShortest (.highlightables >> List.Extra.getAt 1)
-                |> Expect.equal (Just "C")
-    , test "with multiple marked highlightables, selecting the third highlightable, returns the shortest mark type" <|
-        \() ->
-            init
-                [ Highlightable.initInteractive
-                    [ marker (Just "B")
-                    ]
-                    0
-                    "hello"
-                , Highlightable.initInteractive
-                    [ marker (Just "B")
-                    , marker (Just "C")
-                    ]
-                    1
-                    "world"
-                , Highlightable.initInteractive
-                    [ marker (Just "C")
-                    , marker (Just "B")
-                    ]
-                    2
-                    "!"
-                ]
-                |> Highlighter.selectShortest (.highlightables >> List.Extra.getAt 2)
-                |> Expect.equal (Just "C")
-    ]
-
-
 overlappingHighlightTests : List Test
 overlappingHighlightTests =
     let
diff --git a/tests/Spec/Nri/Ui/HighlighterOverlaps.elm b/tests/Spec/Nri/Ui/HighlighterOverlaps.elm
new file mode 100644
index 00000000..ca161ac2
--- /dev/null
+++ b/tests/Spec/Nri/Ui/HighlighterOverlaps.elm
@@ -0,0 +1,145 @@
+module Spec.Nri.Ui.HighlighterOverlaps exposing (spec)
+
+import Expect exposing (Expectation)
+import List.Extra
+import Maybe.Extra
+import Nri.Ui.Colors.V1 as Colors
+import Nri.Ui.Highlightable.V3 as Highlightable
+import Nri.Ui.Highlighter.V5 as Highlighter
+import Nri.Ui.HighlighterTool.V1 as Tool
+import Sort
+import Test exposing (..)
+
+
+spec : Test
+spec =
+    describe "Highlighter#selectShortest"
+        [ test "no overlap" <|
+            \_ ->
+                init2
+                    |> marker "###   "
+                    |> marker "   ***"
+                    |> cursor "   ^  "
+                    |> expect "*"
+        , test "shortest at start" <|
+            \_ ->
+                init2
+                    |> marker "#  "
+                    |> marker "***"
+                    |> cursor "^  "
+                    |> expect "#"
+        , test "shortest in the middle" <|
+            \_ ->
+                init2
+                    |> marker " # "
+                    |> marker "***"
+                    |> cursor " ^ "
+                    |> expect "#"
+        , test "shortest at the end" <|
+            \_ ->
+                init2
+                    |> marker "  #"
+                    |> marker "***"
+                    |> cursor "  ^"
+                    |> expect "#"
+        , test "shortest intersects from left" <|
+            \_ ->
+                init2
+                    |> marker "####  "
+                    |> marker "   ***"
+                    |> cursor "   ^  "
+                    |> expect "*"
+        , test "shortest intersects from right" <|
+            \_ ->
+                init2
+                    |> marker "  ####"
+                    |> marker "***   "
+                    |> cursor "  ^   "
+                    |> expect "*"
+        , test "shortest is non-contiguous" <|
+            \_ ->
+                init2
+                    |> marker "  ####  "
+                    |> marker "*  *   *"
+                    |> cursor "   ^    "
+                    |> expect "*"
+        , test "longest is non-contiguous" <|
+            \_ ->
+                init2
+                    |> marker "      ####      "
+                    |> marker "*****  *   *****"
+                    |> cursor "       ^        "
+                    |> expect "#"
+        ]
+
+
+init2 : String -> String -> String -> Highlighter.Model String
+init2 marker1 marker2 cursor_ =
+    let
+        highlightables =
+            List.Extra.zip (String.toList marker1) (String.toList marker2)
+                |> List.indexedMap
+                    (\idx ( a, b ) ->
+                        Highlightable.initInteractive
+                            (markers a b)
+                            idx
+                            " "
+                    )
+
+        cursorIndex =
+            String.toList cursor_
+                |> List.Extra.elemIndex '^'
+                |> Maybe.withDefault -1
+    in
+    Highlighter.init
+        { id = "test-highlighter-container"
+        , highlightables = highlightables
+        , marker = Tool.Marker (mkMarker "unused")
+        , joinAdjacentInteractiveHighlights = False
+        , sorter = Sort.alphabetical
+        }
+        |> Highlighter.update (Highlighter.Pointer (Highlighter.Over cursorIndex))
+        |> (\( model, _, _ ) -> model)
+
+
+marker : String -> (String -> a) -> a
+marker str f =
+    f str
+
+
+cursor : String -> (String -> a) -> a
+cursor str f =
+    f str
+
+
+expect : String -> Highlighter.Model String -> Expectation
+expect cursorName highlighter =
+    Highlighter.selectShortest Highlighter.hoveredHighlightable highlighter
+        |> Expect.equal (Just cursorName)
+
+
+markers : Char -> Char -> List (Tool.MarkerModel String)
+markers a b =
+    Maybe.Extra.values
+        [ if a == ' ' then
+            Nothing
+
+          else
+            Just (mkMarker (String.fromChar a))
+        , if b == ' ' then
+            Nothing
+
+          else
+            Just (mkMarker (String.fromChar b))
+        ]
+
+
+mkMarker : String -> Tool.MarkerModel String
+mkMarker str =
+    Tool.buildMarker
+        { highlightColor = Colors.magenta
+        , hoverColor = Colors.magenta
+        , hoverHighlightColor = Colors.magenta
+        , kind = str
+        , name = Just str
+        }