diff --git a/bootcommand/boot_command.go b/bootcommand/boot_command.go
index 5fbfeee66..108ff8d9f 100644
--- a/bootcommand/boot_command.go
+++ b/bootcommand/boot_command.go
@@ -601,18 +601,42 @@ var g = &grammar{
 					},
 					&litMatcher{
 						pos:        position{line: 71, col: 11, offset: 1678},
+						val:        "leftcommand",
+						ignoreCase: true,
+						want:       "\"leftCommand\"i",
+					},
+					&litMatcher{
+						pos:        position{line: 71, col: 28, offset: 1695},
+						val:        "rightcommand",
+						ignoreCase: true,
+						want:       "\"rightCommand\"i",
+					},
+					&litMatcher{
+						pos:        position{line: 71, col: 46, offset: 1713},
+						val:        "leftoption",
+						ignoreCase: true,
+						want:       "\"leftOption\"i",
+					},
+					&litMatcher{
+						pos:        position{line: 71, col: 62, offset: 1729},
+						val:        "rightoption",
+						ignoreCase: true,
+						want:       "\"rightOption\"i",
+					},
+					&litMatcher{
+						pos:        position{line: 73, col: 11, offset: 1832},
 						val:        "left",
 						ignoreCase: true,
 						want:       "\"left\"i",
 					},
 					&litMatcher{
-						pos:        position{line: 71, col: 21, offset: 1688},
+						pos:        position{line: 73, col: 21, offset: 1842},
 						val:        "right",
 						ignoreCase: true,
 						want:       "\"right\"i",
 					},
 					&litMatcher{
-						pos:        position{line: 71, col: 32, offset: 1699},
+						pos:        position{line: 73, col: 32, offset: 1853},
 						val:        "menu",
 						ignoreCase: true,
 						want:       "\"menu\"i",
@@ -622,9 +646,9 @@ var g = &grammar{
 		},
 		{
 			name: "NonZeroDigit",
-			pos:  position{line: 73, col: 1, offset: 1708},
+			pos:  position{line: 75, col: 1, offset: 1862},
 			expr: &charClassMatcher{
-				pos:        position{line: 73, col: 16, offset: 1723},
+				pos:        position{line: 75, col: 16, offset: 1877},
 				val:        "[1-9]",
 				ranges:     []rune{'1', '9'},
 				ignoreCase: false,
@@ -633,9 +657,9 @@ var g = &grammar{
 		},
 		{
 			name: "Digit",
-			pos:  position{line: 74, col: 1, offset: 1729},
+			pos:  position{line: 76, col: 1, offset: 1883},
 			expr: &charClassMatcher{
-				pos:        position{line: 74, col: 9, offset: 1737},
+				pos:        position{line: 76, col: 9, offset: 1891},
 				val:        "[0-9]",
 				ranges:     []rune{'0', '9'},
 				ignoreCase: false,
@@ -644,48 +668,48 @@ var g = &grammar{
 		},
 		{
 			name: "TimeUnit",
-			pos:  position{line: 75, col: 1, offset: 1743},
+			pos:  position{line: 77, col: 1, offset: 1897},
 			expr: &choiceExpr{
-				pos: position{line: 75, col: 13, offset: 1755},
+				pos: position{line: 77, col: 13, offset: 1909},
 				alternatives: []interface{}{
 					&litMatcher{
-						pos:        position{line: 75, col: 13, offset: 1755},
+						pos:        position{line: 77, col: 13, offset: 1909},
 						val:        "ns",
 						ignoreCase: false,
 						want:       "\"ns\"",
 					},
 					&litMatcher{
-						pos:        position{line: 75, col: 20, offset: 1762},
+						pos:        position{line: 77, col: 20, offset: 1916},
 						val:        "us",
 						ignoreCase: false,
 						want:       "\"us\"",
 					},
 					&litMatcher{
-						pos:        position{line: 75, col: 27, offset: 1769},
+						pos:        position{line: 77, col: 27, offset: 1923},
 						val:        "µs",
 						ignoreCase: false,
 						want:       "\"µs\"",
 					},
 					&litMatcher{
-						pos:        position{line: 75, col: 34, offset: 1777},
+						pos:        position{line: 77, col: 34, offset: 1931},
 						val:        "ms",
 						ignoreCase: false,
 						want:       "\"ms\"",
 					},
 					&litMatcher{
-						pos:        position{line: 75, col: 41, offset: 1784},
+						pos:        position{line: 77, col: 41, offset: 1938},
 						val:        "s",
 						ignoreCase: false,
 						want:       "\"s\"",
 					},
 					&litMatcher{
-						pos:        position{line: 75, col: 47, offset: 1790},
+						pos:        position{line: 77, col: 47, offset: 1944},
 						val:        "m",
 						ignoreCase: false,
 						want:       "\"m\"",
 					},
 					&litMatcher{
-						pos:        position{line: 75, col: 53, offset: 1796},
+						pos:        position{line: 77, col: 53, offset: 1950},
 						val:        "h",
 						ignoreCase: false,
 						want:       "\"h\"",
@@ -696,11 +720,11 @@ var g = &grammar{
 		{
 			name:        "_",
 			displayName: "\"whitespace\"",
-			pos:         position{line: 77, col: 1, offset: 1802},
+			pos:         position{line: 79, col: 1, offset: 1956},
 			expr: &zeroOrMoreExpr{
-				pos: position{line: 77, col: 19, offset: 1820},
+				pos: position{line: 79, col: 19, offset: 1974},
 				expr: &charClassMatcher{
-					pos:        position{line: 77, col: 19, offset: 1820},
+					pos:        position{line: 79, col: 19, offset: 1974},
 					val:        "[ \\n\\t\\r]",
 					chars:      []rune{' ', '\n', '\t', '\r'},
 					ignoreCase: false,
@@ -710,11 +734,11 @@ var g = &grammar{
 		},
 		{
 			name: "EOF",
-			pos:  position{line: 79, col: 1, offset: 1832},
+			pos:  position{line: 81, col: 1, offset: 1986},
 			expr: &notExpr{
-				pos: position{line: 79, col: 8, offset: 1839},
+				pos: position{line: 81, col: 8, offset: 1993},
 				expr: &anyMatcher{
-					line: 79, col: 9, offset: 1840,
+					line: 81, col: 9, offset: 1994,
 				},
 			},
 		},
diff --git a/bootcommand/boot_command.pigeon b/bootcommand/boot_command.pigeon
index 982e8f98d..35aef33ab 100644
--- a/bootcommand/boot_command.pigeon
+++ b/bootcommand/boot_command.pigeon
@@ -68,6 +68,8 @@ SpecialKey = "bs"i / "del"i / "enter"i / "esc"i / "f10"i / "f11"i / "f12"i
         /  "return"i / "tab"i / "up"i / "down"i / "spacebar"i / "insert"i / "home"i
         / "end"i / "pageUp"i / "pageDown"i / "leftAlt"i / "leftCtrl"i / "leftShift"i
         / "rightAlt"i / "rightCtrl"i / "rightShift"i / "leftSuper"i / "rightSuper"i
+        / "leftCommand"i / "rightCommand"i / "leftOption"i / "rightOption"i
+        // left/right must go last, to not take priority over {left/right}Foo
         / "left"i / "right"i / "menu"i
 
 NonZeroDigit = [1-9]
diff --git a/bootcommand/config.go b/bootcommand/config.go
index e5b13be67..39001f874 100644
--- a/bootcommand/config.go
+++ b/bootcommand/config.go
@@ -64,7 +64,11 @@ const PackerKeyDefault = 100 * time.Millisecond
 //
 // -   `<leftShift> <rightShift>` - Simulates pressing the shift key.
 //
-// -   `<leftSuper> <rightSuper>` - Simulates pressing the ⌘ or Windows key.
+// -   `<leftSuper> <rightSuper>` - Simulates pressing the super key.
+//
+// -   `<leftCommand> <rightCommand>` - Simulates pressing the ⌘ key.
+//
+// -   `<leftOption> <rightOption>` - Simulates pressing the ⌥ key.
 //
 //   - `<wait> <wait5> <wait10>` - Adds a 1, 5 or 10 second pause before
 //     sending any additional keys. This is useful if you have to generally
diff --git a/bootcommand/usb_driver.go b/bootcommand/usb_driver.go
index a49168d26..f42ec9ef2 100644
--- a/bootcommand/usb_driver.go
+++ b/bootcommand/usb_driver.go
@@ -73,6 +73,12 @@ func NewUSBDriver(send SendUsbScanCodes, interval time.Duration) *usbDriver {
 		"leftsuper":  key.CodeLeftGUI,
 		"rightsuper": key.CodeRightGUI,
 		"spacebar":   key.CodeSpacebar,
+
+		// https://developer.apple.com/accessories/Accessory-Design-Guidelines.pdf
+		"leftcommand":  key.CodeLeftGUI,
+		"rightcommand": key.CodeRightGUI,
+		"leftoption":   key.CodeLeftAlt,
+		"rightoption":  key.CodeRightAlt,
 	}
 
 	scancodeIndex := make(map[string]key.Code)
diff --git a/bootcommand/vnc_driver.go b/bootcommand/vnc_driver.go
index 8823897d8..e0119e865 100644
--- a/bootcommand/vnc_driver.go
+++ b/bootcommand/vnc_driver.go
@@ -78,6 +78,12 @@ func NewVNCDriver(c VNCKeyEvent, interval time.Duration) *vncDriver {
 	sMap["tab"] = 0xFF09
 	sMap["up"] = 0xFF52
 
+	// Verified against the built-in VNC server on macOS
+	sMap["leftcommand"] = 0xFFE9
+	sMap["rightcommand"] = 0xFFEA
+	sMap["leftoption"] = 0xFFE7
+	sMap["rightoption"] = 0xFFE8
+
 	return &vncDriver{
 		c:          c,
 		interval:   keyInterval,