diff --git a/CHANGELOG.md b/CHANGELOG.md
index 76fb3117a..a6305e842 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -23,6 +23,10 @@ and this project adheres to [Semantic Versioning](http://semver.org/).
 - Added `switch` attribute to `Switch` events https://github.com/Textualize/textual/pull/1940
 - Breaking change: Added `toggle_button` attribute to RadioButton and Checkbox events, replaces `input` https://github.com/Textualize/textual/pull/1940
 
+### Fixed
+
+- Fixed bug that prevented app pilot to press some keys https://github.com/Textualize/textual/issues/1815
+
 ## [0.13.0] - 2023-03-02
 
 ### Added
diff --git a/src/textual/_xterm_parser.py b/src/textual/_xterm_parser.py
index fc4258390..d232c5a9d 100644
--- a/src/textual/_xterm_parser.py
+++ b/src/textual/_xterm_parser.py
@@ -8,7 +8,7 @@ from . import events, messages
 from ._ansi_sequences import ANSI_SEQUENCES_KEYS
 from ._parser import Awaitable, Parser, TokenCallback
 from ._types import MessageTarget
-from .keys import KEY_NAME_REPLACEMENTS
+from .keys import KEY_NAME_REPLACEMENTS, _character_to_key
 
 # When trying to determine whether the current sequence is a supported/valid
 # escape sequence, at which length should we give up and consider our search
@@ -241,12 +241,7 @@ class XTermParser(Parser[events.Event]):
         elif len(sequence) == 1:
             try:
                 if not sequence.isalnum():
-                    name = (
-                        _unicode_name(sequence)
-                        .lower()
-                        .replace("-", "_")
-                        .replace(" ", "_")
-                    )
+                    name = _character_to_key(sequence)
                 else:
                     name = sequence
                 name = KEY_NAME_REPLACEMENTS.get(name, name)
diff --git a/src/textual/app.py b/src/textual/app.py
index a17a5825b..e7785379a 100644
--- a/src/textual/app.py
+++ b/src/textual/app.py
@@ -70,7 +70,12 @@ from .features import FeatureFlag, parse_features
 from .file_monitor import FileMonitor
 from .filter import LineFilter, Monochrome
 from .geometry import Offset, Region, Size
-from .keys import REPLACED_KEYS, _get_key_display
+from .keys import (
+    REPLACED_KEYS,
+    _character_to_key,
+    _get_key_display,
+    _get_unicode_name_from_key,
+)
 from .messages import CallbackType
 from .reactive import Reactive
 from .renderables.blank import Blank
@@ -865,16 +870,11 @@ class App(Generic[ReturnType], DOMNode):
                 await asyncio.sleep(float(wait_ms) / 1000)
             else:
                 if len(key) == 1 and not key.isalnum():
-                    key = (
-                        unicodedata.name(key)
-                        .lower()
-                        .replace("-", "_")
-                        .replace(" ", "_")
-                    )
+                    key = _character_to_key(key)
                 original_key = REPLACED_KEYS.get(key, key)
                 char: str | None
                 try:
-                    char = unicodedata.lookup(original_key.upper().replace("_", " "))
+                    char = unicodedata.lookup(_get_unicode_name_from_key(original_key))
                 except KeyError:
                     char = key if len(key) == 1 else None
                 print(f"press {key!r} (char={char!r})")
diff --git a/src/textual/keys.py b/src/textual/keys.py
index 1c5fe219d..ef32404d1 100644
--- a/src/textual/keys.py
+++ b/src/textual/keys.py
@@ -211,6 +211,37 @@ KEY_NAME_REPLACEMENTS = {
 }
 REPLACED_KEYS = {value: key for key, value in KEY_NAME_REPLACEMENTS.items()}
 
+# Convert the friendly versions of character key Unicode names
+# back to their original names.
+# This is because we go from Unicode to friendly by replacing spaces and dashes
+# with underscores, which cannot be undone by replacing underscores with spaces/dashes.
+KEY_TO_UNICODE_NAME = {
+    "exclamation_mark": "EXCLAMATION MARK",
+    "quotation_mark": "QUOTATION MARK",
+    "number_sign": "NUMBER SIGN",
+    "dollar_sign": "DOLLAR SIGN",
+    "percent_sign": "PERCENT SIGN",
+    "left_parenthesis": "LEFT PARENTHESIS",
+    "right_parenthesis": "RIGHT PARENTHESIS",
+    "plus_sign": "PLUS SIGN",
+    "hyphen_minus": "HYPHEN-MINUS",
+    "full_stop": "FULL STOP",
+    "less_than_sign": "LESS-THAN SIGN",
+    "equals_sign": "EQUALS SIGN",
+    "greater_than_sign": "GREATER-THAN SIGN",
+    "question_mark": "QUESTION MARK",
+    "commercial_at": "COMMERCIAL AT",
+    "left_square_bracket": "LEFT SQUARE BRACKET",
+    "reverse_solidus": "REVERSE SOLIDUS",
+    "right_square_bracket": "RIGHT SQUARE BRACKET",
+    "circumflex_accent": "CIRCUMFLEX ACCENT",
+    "low_line": "LOW LINE",
+    "grave_accent": "GRAVE ACCENT",
+    "left_curly_bracket": "LEFT CURLY BRACKET",
+    "vertical_line": "VERTICAL LINE",
+    "right_curly_bracket": "RIGHT CURLY BRACKET",
+}
+
 # Some keys have aliases. For example, if you press `ctrl+m` on your keyboard,
 # it's treated the same way as if you press `enter`. Key handlers `key_ctrl_m` and
 # `key_enter` are both valid in this case.
@@ -235,6 +266,14 @@ KEY_DISPLAY_ALIASES = {
 }
 
 
+def _get_unicode_name_from_key(key: str) -> str:
+    """Get the best guess for the Unicode name of the char corresponding to the key.
+
+    This function can be seen as a pseudo-inverse of the function `_character_to_key`.
+    """
+    return KEY_TO_UNICODE_NAME.get(key, key.upper())
+
+
 def _get_key_aliases(key: str) -> list[str]:
     """Return all aliases for the given key, including the key itself"""
     return [key] + KEY_ALIASES.get(key, [])
@@ -249,22 +288,24 @@ def _get_key_display(key: str) -> str:
         return display_alias
 
     original_key = REPLACED_KEYS.get(key, key)
-    upper_original = original_key.upper().replace("_", " ")
+    tentative_unicode_name = _get_unicode_name_from_key(original_key)
     try:
-        unicode_character = unicodedata.lookup(upper_original)
+        unicode_character = unicodedata.lookup(tentative_unicode_name)
     except KeyError:
-        return upper_original
+        return tentative_unicode_name
 
     # Check if printable. `delete` for example maps to a control sequence
     # which we don't want to write to the terminal.
     if unicode_character.isprintable():
         return unicode_character
-    return upper_original
+    return tentative_unicode_name
 
 
 def _character_to_key(character: str) -> str:
-    """Convert a single character to a key value."""
-    assert len(character) == 1
+    """Convert a single character to a key value.
+
+    This transformation can be undone by the function `_get_unicode_name_from_key`.
+    """
     if not character.isalnum():
         key = unicodedata.name(character).lower().replace("-", "_").replace(" ", "_")
     else:

diff --git a/tests/test_pilot.py b/tests/test_pilot.py
new file mode 100644
index 000000000..2ca527895
--- /dev/null
+++ b/tests/test_pilot.py
@@ -0,0 +1,23 @@
+from string import punctuation
+
+from textual import events
+from textual.app import App
+
+KEY_CHARACTERS_TO_TEST = "akTW03" + punctuation.replace("_", "")
+"""Test some "simple" characters (letters + digits) and all punctuation.
+Ignore the underscore because that is an alias to add a pause in the pilot.
+"""
+
+
+async def test_pilot_press_ascii_chars():
+    """Test that the pilot can press most ASCII characters as keys."""
+    keys_pressed = []
+
+    class TestApp(App[None]):
+        def on_key(self, event: events.Key) -> None:
+            keys_pressed.append(event.character)
+
+    async with TestApp().run_test() as pilot:
+        for char in KEY_CHARACTERS_TO_TEST:
+            await pilot.press(char)
+            assert keys_pressed[-1] == char

Pilot cannot press key minus
The way `App._press_keys` is implemented is flawed in here:

https://github.com/Textualize/textual/blob/ba6c8afac6ffb78dffeab9ebdc7c115fd28cd40b/src/textual/app.py#L830-L842

There is a clear bug because the transformation done on `key` with two consecutive replacements cannot be undone in line 840 with a single replacement.
In particular, the keys HYPHEN-MINUS and REVERSE SOLIDUS show that the underscores that we get after the two consecutive replacements cannot be unambiguously reverted.

On top of that, I have to understand what is the issue with a key that has length 1 and is not "alnum".
For example, `"-"` has length 1, is not "alnum", and could very well be pressed as is. Maybe we want to check if `key.isprintable` instead?
tests/test_pilot.py::test_pilot_press_ascii_chars