diff --git a/kmk/common/keycodes.py b/kmk/common/keycodes.py
index 498801b..a1ecbc9 100644
--- a/kmk/common/keycodes.py
+++ b/kmk/common/keycodes.py
@@ -513,11 +513,38 @@ ALL_KEYS = KC = AttrDict({
 })
 
 char_lookup = {
-    "\n": (Keycodes.Common.KC_ENTER,),
-    "\t": (Keycodes.Common.KC_TAB,),
-    ' ': (Keycodes.Common.KC_SPACE,),
-    '-': (Keycodes.Common.KC_MINUS,),
-    '=': (Keycodes.Common.KC_EQUAL,),
-    '+': (Keycodes.Common.KC_EQUAL, Keycodes.Modifiers.KC_LSHIFT),
-    '~': (Keycodes.Common.KC_GRAVE,),
+    "\n": Common.KC_ENTER,
+    "\t": Common.KC_TAB,
+    ' ': Common.KC_SPACE,
+    '-': Common.KC_MINUS,
+    '=': Common.KC_EQUAL,
+    '[': Common.KC_LBRACKET,
+    ']': Common.KC_RBRACKET,
+    "\\": Common.KC_BACKSLASH,
+    ';': Common.KC_SEMICOLON,
+    "'": Common.KC_QUOTE,
+    '`': Common.KC_GRAVE,
+    ',': Common.KC_COMMA,
+    '.': Common.KC_DOT,
+    '~': ShiftedKeycodes.KC_TILDE,
+    '!': ShiftedKeycodes.KC_EXCLAIM,
+    '@': ShiftedKeycodes.KC_AT,
+    '#': ShiftedKeycodes.KC_HASH,
+    '$': ShiftedKeycodes.KC_DOLLAR,
+    '%': ShiftedKeycodes.KC_PERCENT,
+    '^': ShiftedKeycodes.KC_CIRCUMFLEX,
+    '&': ShiftedKeycodes.KC_AMPERSAND,
+    '*': ShiftedKeycodes.KC_ASTERISK,
+    '(': ShiftedKeycodes.KC_LEFT_PAREN,
+    ')': ShiftedKeycodes.KC_RIGHT_PAREN,
+    '_': ShiftedKeycodes.KC_UNDERSCORE,
+    '+': ShiftedKeycodes.KC_PLUS,
+    '{': ShiftedKeycodes.KC_LEFT_CURLY_BRACE,
+    '}': ShiftedKeycodes.KC_RIGHT_CURLY_BRACE,
+    '|': ShiftedKeycodes.KC_PIPE,
+    ':': ShiftedKeycodes.KC_COLON,
+    '"': ShiftedKeycodes.KC_DOUBLE_QUOTE,
+    '<': ShiftedKeycodes.KC_LEFT_ANGLE_BRACKET,
+    '>': ShiftedKeycodes.KC_RIGHT_ANGLE_BRACKET,
+    '?': ShiftedKeycodes.KC_QUESTION,
 }
diff --git a/kmk/common/macros/simple.py b/kmk/common/macros/simple.py
index b901338..91e6680 100644
--- a/kmk/common/macros/simple.py
+++ b/kmk/common/macros/simple.py
@@ -1,5 +1,8 @@
+import string
+
 from kmk.common.event_defs import (hid_report_event, keycode_down_event,
                                    keycode_up_event)
+from kmk.common.keycodes import Keycodes, char_lookup
 from kmk.common.macros import KMKMacro
 
 
@@ -15,3 +18,22 @@ def simple_key_sequence(seq):
                 yield hid_report_event()
 
     return KMKMacro(keydown=_simple_key_sequence)
+
+
+def send_string(message):
+    seq = []
+
+    for char in message:
+        kc = None
+
+        if char in char_lookup:
+            kc = char_lookup[char]
+        elif char in string.ascii_letters + string.digits:
+            kc = getattr(Keycodes.Common, 'KC_{}'.format(char.upper()))
+
+            if char.isupper():
+                kc = Keycodes.Modifiers.KC_LSHIFT(kc)
+
+        seq.append(kc)
+
+    return simple_key_sequence(seq)
diff --git a/kmk/micropython/pyb_hid.py b/kmk/micropython/pyb_hid.py
index 1d6eb72..49e2977 100644
--- a/kmk/micropython/pyb_hid.py
+++ b/kmk/micropython/pyb_hid.py
@@ -1,12 +1,11 @@
 import logging
-import string
 
 from pyb import USB_HID, delay, hid_keyboard
 
 from kmk.common.consts import HID_REPORT_STRUCTURE, HIDReportTypes
 from kmk.common.event_defs import HID_REPORT_EVENT
 from kmk.common.keycodes import (FIRST_KMK_INTERNAL_KEYCODE, ConsumerKeycode,
-                                 Keycodes, ModifierKeycode, char_lookup)
+                                 ModifierKeycode)
 
 
 def generate_pyb_hid_descriptor():
@@ -16,14 +15,6 @@ def generate_pyb_hid_descriptor():
 
 
 class HIDHelper:
-    '''
-    Most methods here return `self` upon completion, allowing chaining:
-
-    ```python
-    myhid = HIDHelper()
-    myhid.send_string('testing').send_string(' ... and testing again')
-    ```
-    '''
     def __init__(self, store, log_level=logging.NOTSET):
         self.logger = logging.getLogger(__name__)
         self.logger.setLevel(log_level)
@@ -111,39 +102,6 @@ class HIDHelper:
 
         return self
 
-    def send_string(self, message):
-        '''
-        Clears the HID report, and sends along a string of arbitrary length.
-        All keys will be removed at the completion of the string. Modifiers
-        are not really supported here, though Shift will be added if
-        necessary to output the key.
-        '''
-
-        self.clear_all()
-        self.send()
-
-        for char in message:
-            kc = None
-            modifier = None
-
-            if char in char_lookup:
-                kc, modifier = char_lookup[char]
-            elif char in string.ascii_letters + string.digits:
-                kc = getattr(Keycodes.Common, 'KC_{}'.format(char.upper()))
-                modifier = Keycodes.Modifiers.KC_SHIFT if char.isupper() else None
-
-            if modifier:
-                self.add_modifier(modifier)
-
-            self.add_key(kc)
-            self.send()
-
-            # Release all keys or we'll forever hold whatever the last keyadd was
-            self.clear_all()
-            self.send()
-
-        return self
-
     def clear_all(self):
         for idx, _ in enumerate(self.report_keys):
             self.report_keys[idx] = 0x00
diff --git a/user_keymaps/klardotsh/threethree_matrix_pyboard.py b/user_keymaps/klardotsh/threethree_matrix_pyboard.py
index 5c27bdb..772a5c8 100644
--- a/user_keymaps/klardotsh/threethree_matrix_pyboard.py
+++ b/user_keymaps/klardotsh/threethree_matrix_pyboard.py
@@ -2,7 +2,7 @@ import machine
 
 from kmk.common.consts import DiodeOrientation, UnicodeModes
 from kmk.common.keycodes import KC
-from kmk.common.macros.simple import simple_key_sequence
+from kmk.common.macros.simple import send_string, simple_key_sequence
 from kmk.common.macros.unicode import unicode_sequence
 from kmk.entrypoints.handwire.pyboard import main
 
@@ -13,7 +13,7 @@ rows = (p.X1, p.X2, p.X3)
 diode_orientation = DiodeOrientation.COLUMNS
 unicode_mode = UnicodeModes.LINUX
 
-MACRO_TEST_STRING = simple_key_sequence([
+MACRO_TEST_SIMPLE = simple_key_sequence([
     KC.LSHIFT(KC.H),
     KC.E,
     KC.L,
@@ -28,6 +28,8 @@ MACRO_TEST_STRING = simple_key_sequence([
     KC.EXCLAIM,
 ])
 
+MACRO_TEST_STRING = send_string("Hello! from, uhhhh, send_string | and some other WEIRD STUFF`  \\ like this' \"\t[]")
+
 ANGRY_TABLE_FLIP = unicode_sequence([
     "28",
     "30ce",
@@ -55,7 +57,7 @@ keymap = [
     ],
     [
         [KC.VOLU, KC.MUTE, ANGRY_TABLE_FLIP],
-        [KC.TRNS, KC.PIPE, KC.MEDIA_PLAY_PAUSE],
+        [KC.TRNS, KC.PIPE, MACRO_TEST_SIMPLE],
         [KC.VOLD, KC.P,    MACRO_TEST_STRING],
     ],
     [