diff --git a/lib/models/state.js b/lib/models/state.js
index 70ff2063c..f2ae395ab 100644
--- a/lib/models/state.js
+++ b/lib/models/state.js
@@ -21,7 +21,7 @@ const History = new Record({
  */
 
 const DEFAULTS = {
-  cursorMarks: new Set(),
+  cursorMarks: null,
   document: new Document(),
   selection: new Selection(),
   history: new History(),
@@ -285,10 +285,7 @@ class State extends new Record(DEFAULTS) {
    */
 
   get marks() {
-    const set = this.document.getMarksAtRange(this.selection)
-    return this.selection.isExpanded
-      ? set
-      : set.union(this.cursorMarks)
+    return this.cursorMarks || this.document.getMarksAtRange(this.selection)
   }
 
   /**
@@ -674,27 +671,15 @@ class State extends new Record(DEFAULTS) {
 
     // Determine what the selection should be after inserting.
     if (selection.isExpanded) {
-      after = selection
-        .collapseToStart()
-        .moveForward(text.length)
+      after = selection.collapseToStart().moveForward(text.length)
     }
 
     else {
       after = selection.moveForward(text.length)
     }
 
-    // Insert the text.
-    document = document.insertTextAtRange(selection, text)
-
-    // If there are any marks on the cursor, apply them.
-    if (cursorMarks.size) {
-      const range = after.extendBackward(text.length).normalize(document)
-      cursorMarks.forEach((mark) => {
-        document = document.markAtRange(range, mark)
-      })
-    }
-
-    // Update the selection and the state.
+    // Insert the text and update the selection.
+    document = document.insertTextAtRange(selection, text, cursorMarks)
     selection = after
     state = state.merge({ document, selection })
     return state
@@ -714,8 +699,9 @@ class State extends new Record(DEFAULTS) {
     // If the selection is collapsed, add the mark to the cursor instead.
     if (selection.isCollapsed) {
       if (typeof mark == 'string') mark = new Mark({ type: mark })
-      cursorMarks = cursorMarks.add(mark)
-      return state.merge({ cursorMarks })
+      const marks = document.getMarksAtRange(selection)
+      state = state.merge({ cursorMarks: marks.add(mark) })
+      return state
     }
 
     document = document.markAtRange(selection, mark)
@@ -839,8 +825,9 @@ class State extends new Record(DEFAULTS) {
     // If the selection is collapsed, remove the mark from the cursor instead.
     if (selection.isCollapsed) {
       if (typeof mark == 'string') mark = new Mark({ type: mark })
-      cursorMarks = cursorMarks.remove(mark)
-      return state.merge({ cursorMarks })
+      const marks = document.getMarksAtRange(selection)
+      state = state.merge({ cursorMarks: marks.remove(mark) })
+      return state
     }
 
     document = document.unmarkAtRange(selection, mark)
diff --git a/lib/models/text.js b/lib/models/text.js
index 82e03405b..5895ad23c 100644
--- a/lib/models/text.js
+++ b/lib/models/text.js
@@ -110,15 +110,20 @@ class Text extends new Record(DEFAULTS) {
   /**
    * Insert text `string` at `index`.
    *
-   * @param {String} string
    * @param {Numbder} index
+   * @param {String} string
+   * @param {String} marks (optional)
    * @return {Text} text
    */
 
-  insertText(string, index) {
+  insertText(index, string, marks) {
     let { characters } = this
-    const prev = index ? characters.get(index - 1) : null
-    const marks = prev ? prev.marks : Mark.createSet()
+
+    if (!marks) {
+      const prev = index ? characters.get(index - 1) : null
+      marks = prev ? prev.marks : Mark.createSet()
+    }
+
     const chars = Character.createList(string.split('').map((char) => {
       return {
         text: char,
diff --git a/lib/models/transform.js b/lib/models/transform.js
index 2b49d61bb..260c813a7 100644
--- a/lib/models/transform.js
+++ b/lib/models/transform.js
@@ -188,8 +188,9 @@ class Transform extends new Record(DEFAULT_PROPERTIES) {
 
     // If the selection has changed, clear any existing cursor marks.
     if (state.selection != selection) {
-      cursorMarks = cursorMarks.clear()
-      state = state.merge({ cursorMarks })
+      state = state.merge({
+        cursorMarks: null
+      })
     }
 
     // Apply the "isNative" flag, which is used to allow for natively-handled
diff --git a/lib/models/transforms.js b/lib/models/transforms.js
index 3982a0b88..cfe9ad4d3 100644
--- a/lib/models/transforms.js
+++ b/lib/models/transforms.js
@@ -268,14 +268,15 @@ const Transforms = {
   },
 
   /**
-   * Insert text `string` at a `range`.
+   * Insert text `string` at a `range`, with optional `marks`.
    *
    * @param {Selection} range
    * @param {String} string
+   * @param {Set} marks (optional)
    * @return {Node} node
    */
 
-  insertTextAtRange(range, string) {
+  insertTextAtRange(range, string, marks) {
     let node = this
 
     // When still expanded, remove the current range first.
@@ -287,7 +288,7 @@ const Transforms = {
     // Insert text at the range's offset.
     const { startKey, startOffset } = range
     let text = node.getDescendant(startKey)
-    text = text.insertText(string, startOffset)
+    text = text.insertText(startOffset, string, marks)
     node = node.updateDescendant(text)
 
     return node
diff --git a/test/transforms/fixtures/mark/collapsed-selection-off-again/index.js b/test/transforms/fixtures/mark/collapsed-selection-off-again/index.js
new file mode 100644
index 000000000..962dc40e3
--- /dev/null
+++ b/test/transforms/fixtures/mark/collapsed-selection-off-again/index.js
@@ -0,0 +1,20 @@
+
+export default function (state) {
+  const { document, selection } = state
+  const texts = document.getTextNodes()
+  const first = texts.first()
+
+  return state
+    .transform()
+    .moveTo({
+      anchorKey: first.key,
+      anchorOffset: 0,
+      focusKey: first.key,
+      focusOffset: 0
+    })
+    .mark('bold')
+    .insertText('a')
+    .unmark('bold')
+    .insertText('b')
+    .apply()
+}
diff --git a/test/transforms/fixtures/mark/collapsed-selection-off-again/input.yaml b/test/transforms/fixtures/mark/collapsed-selection-off-again/input.yaml
new file mode 100644
index 000000000..b1be31e90
--- /dev/null
+++ b/test/transforms/fixtures/mark/collapsed-selection-off-again/input.yaml
@@ -0,0 +1,8 @@
+
+nodes:
+  - kind: block
+    type: paragraph
+    nodes:
+      - kind: text
+        ranges:
+          - text: word
diff --git a/test/transforms/fixtures/mark/collapsed-selection-off-again/output.yaml b/test/transforms/fixtures/mark/collapsed-selection-off-again/output.yaml
new file mode 100644
index 000000000..94704aa20
--- /dev/null
+++ b/test/transforms/fixtures/mark/collapsed-selection-off-again/output.yaml
@@ -0,0 +1,11 @@
+
+nodes:
+  - kind: block
+    type: paragraph
+    nodes:
+      - kind: text
+        ranges:
+          - text: a
+            marks:
+              - type: bold
+          - text: bword