diff --git a/spec/app/edit-session-spec.coffee b/spec/app/edit-session-spec.coffee
index 494b6e0ec..aa691496e 100644
--- a/spec/app/edit-session-spec.coffee
+++ b/spec/app/edit-session-spec.coffee
@@ -1225,10 +1225,10 @@ describe "EditSession", ->
         describe "when autoIndent is enabled", ->
           describe "when the cursor's column is less than the suggested level of indentation", ->
             describe "when 'softTabs' is true (the default)", ->
-              it "inserts enough whitespace to bring the line to the suggested level of indentaion", ->
+              it "moves the cursor to the end of the leading whitespace and inserts enough whitespace to bring the line to the suggested level of indentaion", ->
                 buffer.insert([5, 0], "  \n")
                 editSession.tabLength = 2
-                editSession.setCursorBufferPosition [5, 2]
+                editSession.setCursorBufferPosition [5, 0]
                 editSession.setAutoIndent(true)
                 editSession.indent()
                 expect(buffer.lineForRow(5)).toMatch /^\s+$/
@@ -1236,22 +1236,22 @@ describe "EditSession", ->
                 expect(editSession.getCursorBufferPosition()).toEqual [5, 6]
 
             describe "when 'softTabs' is false", ->
-              it "inserts enough tabs to bring the line to the suggested level of indentaion", ->
+              it "moves the cursor to the end of the leading whitespace and inserts enough tabs to bring the line to the suggested level of indentaion", ->
                 convertToHardTabs(buffer)
                 editSession.softTabs = false
                 buffer.insert([5, 0], "\t\n")
-                editSession.setCursorBufferPosition [5, 1]
+                editSession.setCursorBufferPosition [5, 0]
                 editSession.setAutoIndent(true)
                 editSession.indent()
                 expect(buffer.lineForRow(5)).toMatch /^\t\t\t$/
                 expect(editSession.getCursorBufferPosition()).toEqual [5, 3]
 
-          describe "when the cursor's column is greater than the suggested level of indentation", ->
+          describe "when the line's indent level is greater than the suggested level of indentation", ->
             describe "when 'softTabs' is true (the default)", ->
-              it "inserts 'tabLength' spaces into the buffer", ->
+              it "moves the cursor to the end of the leading whitespace and inserts 'tabLength' spaces into the buffer", ->
                 buffer.insert([7, 0], "      \n")
                 editSession.tabLength = 2
-                editSession.setCursorBufferPosition [7, 6]
+                editSession.setCursorBufferPosition [7, 2]
                 editSession.setAutoIndent(true)
                 editSession.indent()
                 expect(buffer.lineForRow(7)).toMatch /^\s+$/
@@ -1259,11 +1259,11 @@ describe "EditSession", ->
                 expect(editSession.getCursorBufferPosition()).toEqual [7, 8]
 
             describe "when 'softTabs' is false", ->
-              it "inserts \t into the buffer", ->
+              it "moves the cursor to the end of the leading whitespace and inserts \t into the buffer", ->
                 convertToHardTabs(buffer)
                 editSession.softTabs = false
                 buffer.insert([7, 0], "\t\t\t\n")
-                editSession.setCursorBufferPosition [7, 3]
+                editSession.setCursorBufferPosition [7, 1]
                 editSession.setAutoIndent(true)
                 editSession.indent()
                 expect(buffer.lineForRow(7)).toMatch /^\t\t\t\t$/
diff --git a/src/app/cursor.coffee b/src/app/cursor.coffee
index 315be7fd8..327d6e2a8 100644
--- a/src/app/cursor.coffee
+++ b/src/app/cursor.coffee
@@ -111,6 +111,15 @@ class Cursor
     newPosition = [position.row, 0] if newPosition.isEqual(position)
     @setBufferPosition(newPosition)
 
+  skipLeadingWhitespace: ->
+    position = @getBufferPosition()
+    range = @editSession.bufferRangeForBufferRow(position.row)
+    endOfLeadingWhitespace = null
+    @editSession.scanInRange /^[ \t]*/, range, (match, matchRange) =>
+      endOfLeadingWhitespace = matchRange.end
+
+    @setBufferPosition(endOfLeadingWhitespace) if endOfLeadingWhitespace.isGreaterThan(position)
+
   moveToEndOfLine: ->
     @setBufferPosition([@getBufferRow(), Infinity])
 
diff --git a/src/app/selection.coffee b/src/app/selection.coffee
index d0123566b..17066e120 100644
--- a/src/app/selection.coffee
+++ b/src/app/selection.coffee
@@ -187,6 +187,7 @@ class Selection
     { row, column } = @cursor.getBufferPosition()
 
     if @isEmpty()
+      @cursor.skipLeadingWhitespace()
       desiredIndent = @editSession.suggestedIndentForBufferRow(row)
       delta = desiredIndent - @cursor.getIndentLevel()