diff --git a/src/SelectionManager.test.ts b/src/SelectionManager.test.ts
index e0ff6789..eb9322b6 100644
--- a/src/SelectionManager.test.ts
+++ b/src/SelectionManager.test.ts
@@ -142,6 +142,49 @@ describe('SelectionManager', () => {
       selectionManager.selectWordAt([14, 0]);
       assert.equal(selectionManager.selectionText, 'foo');
     });
+    it('should select up to non-path characters that are commonly adjacent to paths', () => {
+      buffer.push(stringToRow(':ab:(cd)[ef]{gh}\'ij"'));
+      selectionManager.selectWordAt([0, 0]);
+      assert.equal(selectionManager.selectionText, ':ab');
+      selectionManager.selectWordAt([1, 0]);
+      assert.equal(selectionManager.selectionText, 'ab');
+      selectionManager.selectWordAt([2, 0]);
+      assert.equal(selectionManager.selectionText, 'ab');
+      selectionManager.selectWordAt([3, 0]);
+      assert.equal(selectionManager.selectionText, 'ab:');
+      selectionManager.selectWordAt([4, 0]);
+      assert.equal(selectionManager.selectionText, '(cd');
+      selectionManager.selectWordAt([5, 0]);
+      assert.equal(selectionManager.selectionText, 'cd');
+      selectionManager.selectWordAt([6, 0]);
+      assert.equal(selectionManager.selectionText, 'cd');
+      selectionManager.selectWordAt([7, 0]);
+      assert.equal(selectionManager.selectionText, 'cd)');
+      selectionManager.selectWordAt([8, 0]);
+      assert.equal(selectionManager.selectionText, '[ef');
+      selectionManager.selectWordAt([9, 0]);
+      assert.equal(selectionManager.selectionText, 'ef');
+      selectionManager.selectWordAt([10, 0]);
+      assert.equal(selectionManager.selectionText, 'ef');
+      selectionManager.selectWordAt([11, 0]);
+      assert.equal(selectionManager.selectionText, 'ef]');
+      selectionManager.selectWordAt([12, 0]);
+      assert.equal(selectionManager.selectionText, '{gh');
+      selectionManager.selectWordAt([13, 0]);
+      assert.equal(selectionManager.selectionText, 'gh');
+      selectionManager.selectWordAt([14, 0]);
+      assert.equal(selectionManager.selectionText, 'gh');
+      selectionManager.selectWordAt([15, 0]);
+      assert.equal(selectionManager.selectionText, 'gh}');
+      selectionManager.selectWordAt([16, 0]);
+      assert.equal(selectionManager.selectionText, '\'ij');
+      selectionManager.selectWordAt([17, 0]);
+      assert.equal(selectionManager.selectionText, 'ij');
+      selectionManager.selectWordAt([18, 0]);
+      assert.equal(selectionManager.selectionText, 'ij');
+      selectionManager.selectWordAt([19, 0]);
+      assert.equal(selectionManager.selectionText, 'ij"');
+    });
   });
 
   describe('_selectLineAt', () => {
diff --git a/src/SelectionManager.ts b/src/SelectionManager.ts
index ac0e4290..a769afd1 100644
--- a/src/SelectionManager.ts
+++ b/src/SelectionManager.ts
@@ -37,6 +37,12 @@ const CLEAR_MOUSE_DOWN_TIME = 400;
  */
 const CLEAR_MOUSE_DISTANCE = 10;
 
+/**
+ * A string containing all characters that are considered word separated by the
+ * double click to select work logic.
+ */
+const WORD_SEPARATORS = ' ()[]{}:\'"';
+
 // TODO: Move these constants elsewhere, they belong in a buffer or buffer
 //       data/line class.
 const LINE_DATA_CHAR_INDEX = 1;
@@ -326,7 +332,7 @@ export class SelectionManager extends EventEmitter {
    * @param event The mouse event.
    */
   private _getMouseBufferCoords(event: MouseEvent): [number, number] {
-    const coords = Mouse.getCoords(event, this._rowContainer, this._charMeasure, this._terminal.cols, this._terminal.rows);
+    const coords = Mouse.getCoords(event, this._rowContainer, this._charMeasure, this._terminal.cols, this._terminal.rows, true);
     // Convert to 0-based
     coords[0]--;
     coords[1]--;
@@ -629,7 +635,7 @@ export class SelectionManager extends EventEmitter {
         endCol++;
       }
       // Expand the string in both directions until a space is hit
-      while (startIndex > 0 && line.charAt(startIndex - 1) !== ' ') {
+      while (startIndex > 0 && !this._isCharWordSeparator(line.charAt(startIndex - 1))) {
         if (bufferLine[startCol - 1][LINE_DATA_WIDTH_INDEX] === 0) {
           // If the next character is a wide char, record it and skip the column
           leftWideCharCount++;
@@ -638,7 +644,7 @@ export class SelectionManager extends EventEmitter {
         startIndex--;
         startCol--;
       }
-      while (endIndex + 1 < line.length && line.charAt(endIndex + 1) !== ' ') {
+      while (endIndex + 1 < line.length && !this._isCharWordSeparator(line.charAt(endIndex + 1))) {
         if (bufferLine[endCol + 1][LINE_DATA_WIDTH_INDEX] === 2) {
           // If the next character is a wide char, record it and skip the column
           rightWideCharCount++;
@@ -673,6 +679,15 @@ export class SelectionManager extends EventEmitter {
     this._model.selectionEnd = [this._model.areSelectionValuesReversed() ? wordPosition.start : (wordPosition.start + wordPosition.length), coords[1]];
   }
 
+  /**
+   * Gets whether the character is considered a word separator by the select
+   * word logic.
+   * @param char The character to check.
+   */
+  private _isCharWordSeparator(char: string): boolean {
+    return WORD_SEPARATORS.indexOf(char) >= 0;
+  }
+
   /**
    * Selects the line specified.
    * @param line The line index.
diff --git a/src/utils/Mouse.ts b/src/utils/Mouse.ts
index 79c5d5c1..a5d72c1e 100644
--- a/src/utils/Mouse.ts
+++ b/src/utils/Mouse.ts
@@ -30,12 +30,17 @@ export function getCoordsRelativeToElement(event: MouseEvent, element: HTMLEleme
  * @param event The mouse event.
  * @param rowContainer The terminal's row container.
  * @param charMeasure The char measure object used to determine character sizes.
+ * @param colCount The number of columns in the terminal.
+ * @param rowCount The number of rows n the terminal.
+ * @param isSelection Whether the request is for the selection or not. This will
+ * apply an offset to the x value such that the left half of the cell will
+ * select that cell and the right half will select the next cell.
  */
-export function getCoords(event: MouseEvent, rowContainer: HTMLElement, charMeasure: CharMeasure, colCount: number, rowCount: number): [number, number] {
+export function getCoords(event: MouseEvent, rowContainer: HTMLElement, charMeasure: CharMeasure, colCount: number, rowCount: number, isSelection?: boolean): [number, number] {
   const coords = getCoordsRelativeToElement(event, rowContainer);
 
-  // Convert to cols/rows
-  coords[0] = Math.ceil(coords[0] / charMeasure.width);
+  // Convert to cols/rows.
+  coords[0] = Math.ceil((coords[0] + (isSelection ? charMeasure.width / 2 : 0)) / charMeasure.width);
   coords[1] = Math.ceil(coords[1] / charMeasure.height);
 
   // Ensure coordinates are within the terminal viewport.