diff --git a/tests/Spec/Nri/Ui/Highlightable.elm b/tests/Spec/Nri/Ui/Highlightable.elm
index 50afa683..e8146236 100644
--- a/tests/Spec/Nri/Ui/Highlightable.elm
+++ b/tests/Spec/Nri/Ui/Highlightable.elm
@@ -3,7 +3,8 @@ module Spec.Nri.Ui.Highlightable exposing (spec)
 import Expect
 import Fuzz exposing (..)
 import Nri.Ui.Colors.V1 as Colors
-import Nri.Ui.Highlightable.V1 as Highlightable
+import Nri.Ui.Highlightable.V1 as HighlightableV1
+import Nri.Ui.Highlightable.V2 as Highlightable
 import Nri.Ui.Highlighter.V2 as Highlighter
 import Nri.Ui.HighlighterTool.V1 as Tool
 import String.Extra
@@ -20,7 +21,7 @@ spec =
                         fragment =
                             strings
                                 |> List.map (Tuple.pair [])
-                                |> Highlightable.initFragment Nothing 0
+                                |> HighlightableV1.initFragment Nothing 0
 
                         roundtripText =
                             Highlighter.asFragmentTuples fragment
@@ -48,13 +49,78 @@ spec =
                                )
                             |> max 0
                 in
-                Highlightable.splitWords a
+                HighlightableV1.splitWords a
                     |> List.length
                     |> Expect.equal expected
+        , describe "HighlightableV1.fromMarkdown" fromMarkdownV1Spec
         , describe "fromMarkdown" fromMarkdownSpec
         ]
 
 
+fromMarkdownV1Spec : List Test
+fromMarkdownV1Spec =
+    let
+        testFromMarkdown startingString expected =
+            HighlightableV1.fromMarkdown startingString
+                |> List.map (\{ text, marked } -> ( text, marked ))
+                |> Expect.equal expected
+
+        defaultMark =
+            Tool.buildMarker
+                { highlightColor = Colors.highlightYellow
+                , hoverColor = Colors.highlightYellow
+                , hoverHighlightColor = Colors.highlightYellow
+                , kind = ()
+                , name = Nothing
+                }
+    in
+    [ test "with an empty string, produces empty list of Highlightables" <|
+        \() ->
+            testFromMarkdown "" []
+    , test "does not mark non-highlighted content" <|
+        \() ->
+            testFromMarkdown "A sentence without highlighted content"
+                [ ( "A sentence without highlighted content", Nothing ) ]
+    , test "does not strip emphasized content" <|
+        \() ->
+            testFromMarkdown "A *sentence without* **highlighted content**"
+                [ ( "A *sentence without* **highlighted content**", Nothing ) ]
+    , test "marks a single segment as highlighted" <|
+        \() ->
+            testFromMarkdown "[fake link]()"
+                [ ( "fake link", Just defaultMark ) ]
+    , test "does mark content that's intended to be highlighted" <|
+        \() ->
+            testFromMarkdown "A sentence with [highlighted content]()"
+                [ ( "A sentence with ", Nothing )
+                , ( "highlighted content", Just defaultMark )
+                ]
+    , test "marks content that's intended to be highlighted within an emphasis" <|
+        \() ->
+            testFromMarkdown "A sentence with *emphasized [highlighted content]()!*"
+                [ ( "A sentence with *emphasized *", Nothing )
+                , ( "*highlighted content*", Just defaultMark )
+                , ( "*!*", Nothing )
+                ]
+    , test "marks content that's intended to be highlighted that also contains an emphasis" <|
+        \() ->
+            testFromMarkdown "A sentence with [highlighted *and partially emphasized* content]()"
+                [ ( "A sentence with ", Nothing )
+                , ( "highlighted *and partially emphasized* content", Just defaultMark )
+                ]
+    , test "does not highlight actual links" <|
+        \() ->
+            testFromMarkdown "I am a [real link](google.com)"
+                [ ( "I am a [real link](google.com)", Nothing )
+                ]
+    , test "does not get confused by parentheses" <|
+        \() ->
+            testFromMarkdown "main thought (parenthetical)"
+                [ ( "main thought (parenthetical)", Nothing )
+                ]
+    ]
+
+
 fromMarkdownSpec : List Test
 fromMarkdownSpec =
     let