diff --git a/src/main/scala/ocelot/desktop/ui/widget/TextInput.scala b/src/main/scala/ocelot/desktop/ui/widget/TextInput.scala
index 3de6af8..c25b1b6 100644
--- a/src/main/scala/ocelot/desktop/ui/widget/TextInput.scala
+++ b/src/main/scala/ocelot/desktop/ui/widget/TextInput.scala
@@ -8,7 +8,7 @@ import ocelot.desktop.ui.UiHandler
 import ocelot.desktop.ui.event.handlers.MouseHandler
 import ocelot.desktop.ui.event.sources.KeyEvents
 import ocelot.desktop.ui.event.{DragEvent, KeyEvent, MouseEvent}
-import ocelot.desktop.ui.widget.TextInput.{Cursor, Selection, Text}
+import ocelot.desktop.ui.widget.TextInput.{Cursor, Selection, Text, isPunctuation}
 import ocelot.desktop.ui.widget.contextmenu.{ContextMenu, ContextMenuEntry}
 import ocelot.desktop.ui.widget.traits.HoverAnimation
 import ocelot.desktop.util.NumberUtils.ExtendedInt
@@ -209,7 +209,7 @@ class TextInput(val initialText: String = "") extends Widget with MouseHandler w
     case event @ KeyEvent(KeyEvent.State.Press | KeyEvent.State.Repeat, Keyboard.KEY_LEFT, _) if isFocused =>
       handleKeyMovement(selection match {
         case Some(Selection.Ordered(start, _)) if !KeyEvents.isShiftDown => start
-        case _ if KeyEvents.isControlDown => findWordBoundary(cursor.position - 1, forward = false, wordStart = true)
+        case _ if KeyEvents.isControlDown => findWordBoundary(cursor.position - 1, forward = false, wordStart = true, punctuationBoundaries = false)
         case _ => cursor.position - 1
       })
 
@@ -218,7 +218,7 @@ class TextInput(val initialText: String = "") extends Widget with MouseHandler w
     case event @ KeyEvent(KeyEvent.State.Press | KeyEvent.State.Repeat, Keyboard.KEY_RIGHT, _) if isFocused =>
       handleKeyMovement(selection match {
         case Some(Selection.Ordered(_, end)) if !KeyEvents.isShiftDown => end
-        case _ if KeyEvents.isControlDown => findWordBoundary(cursor.position + 1, forward = true, wordStart = false)
+        case _ if KeyEvents.isControlDown => findWordBoundary(cursor.position + 1, forward = true, wordStart = false, punctuationBoundaries = false)
         case _ => cursor.position + 1
       })
 
@@ -237,7 +237,7 @@ class TextInput(val initialText: String = "") extends Widget with MouseHandler w
         deleteSelection()
       } else {
         val start = if (KeyEvents.isControlDown) {
-          findWordBoundary(cursor.position - 1, forward = false, wordStart = true)
+          findWordBoundary(cursor.position - 1, forward = false, wordStart = true, punctuationBoundaries = false)
         } else {
           (cursor.position - 1).clamped(0, _text.chars.length)
         }
@@ -253,7 +253,7 @@ class TextInput(val initialText: String = "") extends Widget with MouseHandler w
         deleteSelection()
       } else {
         val end = if (KeyEvents.isControlDown) {
-          findWordBoundary(cursor.position + 1, forward = true, wordStart = false)
+          findWordBoundary(cursor.position + 1, forward = true, wordStart = false, punctuationBoundaries = false)
         } else {
           (cursor.position + 1).clamped(0, _text.chars.length)
         }
@@ -344,9 +344,12 @@ class TextInput(val initialText: String = "") extends Widget with MouseHandler w
     * If `wordStart` is `true`, the word boundary begins a word. Otherwise, it ends a word (one past the last character
     * of the word). If no boundary is found, the function returns the furthest index in the specified direction.
     * 
+    * If `punctuationBoundaries` is enabled, a contiguous punctuation sequence is treated as a word for the purposes of
+    * boundary search.
+    * 
     * May return the `initialPosition` if it's already at the boundary.
     */
-  private def findWordBoundary(initialPosition: Int, forward: Boolean, wordStart: Boolean): Int = {
+  private def findWordBoundary(initialPosition: Int, forward: Boolean, wordStart: Boolean, punctuationBoundaries: Boolean): Int = {
     import Character.isLetterOrDigit
     
     val start = initialPosition.clamped(0, _text.chars.length)
@@ -358,9 +361,15 @@ class TextInput(val initialText: String = "") extends Widget with MouseHandler w
     }
     
     val isBoundaryCodepoints: (Int, Int) => Boolean = if (wordStart) {
-      (prev, current) => !isLetterOrDigit(prev) && isLetterOrDigit(current)
+      (prev, current) => (
+        isLetterOrDigit(current) && !isLetterOrDigit(prev)
+          || punctuationBoundaries && isPunctuation(current) && !isPunctuation(prev)
+      )
     } else {
-      (prev, current) => isLetterOrDigit(prev) && !isLetterOrDigit(current)
+      (prev, current) => (
+        !isLetterOrDigit(current) && isLetterOrDigit(prev)
+          || punctuationBoundaries && !isPunctuation(current) && isPunctuation(prev)
+      )
     }
 
     def isBoundary(idx: Int): Boolean = {
@@ -371,8 +380,8 @@ class TextInput(val initialText: String = "") extends Widget with MouseHandler w
   }
 
   private def selectWord(): Unit = {
-    val from = findWordBoundary(cursor.position, forward = false, wordStart = true)
-    val to = findWordBoundary(cursor.position, forward = true, wordStart = false)
+    val from = findWordBoundary(cursor.position, forward = false, wordStart = true, punctuationBoundaries = true)
+    val to = findWordBoundary(from + 1, forward = true, wordStart = false, punctuationBoundaries = true)
     selection = Selection(from, to)
   }
 
@@ -507,6 +516,20 @@ class TextInput(val initialText: String = "") extends Widget with MouseHandler w
 }
 
 object TextInput {
+  private val PunctuationCategories = Array[Int](
+    Character.CONNECTOR_PUNCTUATION,
+    Character.DASH_PUNCTUATION,
+    Character.END_PUNCTUATION,
+    Character.FINAL_QUOTE_PUNCTUATION,
+    Character.INITIAL_QUOTE_PUNCTUATION,
+    Character.OTHER_PUNCTUATION,
+    Character.START_PUNCTUATION,
+  )
+
+  private def isPunctuation(codepoint: Int): Boolean = {
+    PunctuationCategories.contains(Character.getType(codepoint))
+  }
+
   class Text(initialValue: Array[Int]) extends BaseWatcher(initialValue) {
     def chars: Array[Int] = value
     def chars_=(newValue: Array[Int]): Unit = value = newValue