diff --git a/src/goose/cli/prompt/create.py b/src/goose/cli/prompt/create.py
index 628c86ccb..899890824 100644
--- a/src/goose/cli/prompt/create.py
+++ b/src/goose/cli/prompt/create.py
@@ -6,10 +6,16 @@
 
 from goose.cli.prompt.completer import GoosePromptCompleter
 from goose.cli.prompt.lexer import PromptLexer
-from goose.command import get_commands
+from goose.command.base import Command
 
 
-def create_prompt() -> PromptSession:
+def create_prompt(commands: dict[str, Command]) -> PromptSession:
+    """
+    Create a prompt session with the given commands.
+
+    Args:
+        commands (dict[str, Command]): A dictionary of command names, and instances of Command classes.
+    """
     # Define custom style
     style = Style.from_dict(
         {
@@ -52,12 +58,6 @@ def _(event: KeyPressEvent) -> None:
                 # accept completion
                 buffer.complete_state = None
 
-    # instantiate the commands available in the prompt
-    commands = dict()
-    command_plugins = get_commands()
-    for command, command_cls in command_plugins.items():
-        commands[command] = command_cls()
-
     return PromptSession(
         completer=GoosePromptCompleter(commands=commands),
         lexer=PromptLexer(list(commands.keys())),
diff --git a/src/goose/cli/prompt/goose_prompt_session.py b/src/goose/cli/prompt/goose_prompt_session.py
index cfcedd80a..14b2cef54 100644
--- a/src/goose/cli/prompt/goose_prompt_session.py
+++ b/src/goose/cli/prompt/goose_prompt_session.py
@@ -1,34 +1,84 @@
 from typing import Optional
 
 from prompt_toolkit import PromptSession
+from prompt_toolkit.document import Document
 from prompt_toolkit.formatted_text import FormattedText
 from prompt_toolkit.validation import DummyValidator
 
 from goose.cli.prompt.create import create_prompt
+from goose.cli.prompt.lexer import PromptLexer
 from goose.cli.prompt.prompt_validator import PromptValidator
 from goose.cli.prompt.user_input import PromptAction, UserInput
+from goose.command import get_commands
 
 
 class GoosePromptSession:
-    def __init__(self, prompt_session: PromptSession) -> None:
-        self.prompt_session = prompt_session
+    def __init__(self) -> None:
+        # instantiate the commands available in the prompt
+        self.commands = dict()
+        command_plugins = get_commands()
+        for command, command_cls in command_plugins.items():
+            self.commands[command] = command_cls()
+        self.main_prompt_session = create_prompt(self.commands)
+        self.text_prompt_session = PromptSession()
 
-    @staticmethod
-    def create_prompt_session() -> "GoosePromptSession":
-        return GoosePromptSession(create_prompt())
+    def get_message_after_commands(self, message: str) -> str:
+        lexer = PromptLexer(command_names=list(self.commands.keys()))
+        doc = Document(message)
+        lines = []
+        # iterate through each line of the document
+        for line_num in range(len(doc.lines)):
+            classes_in_line = lexer.lex_document(doc)(line_num)
+            line_result = []
+            i = 0
+            while i < len(classes_in_line):
+                # if a command is found and it is not the last part of the line
+                if classes_in_line[i][0] == "class:command" and i + 1 < len(classes_in_line):
+                    # extract the command name
+                    command_name = classes_in_line[i][1].strip("/").strip(":")
+                    # get the value following the command
+                    if classes_in_line[i + 1][0] == "class:parameter":
+                        command_value = classes_in_line[i + 1][1]
+                    else:
+                        command_value = ""
+
+                    # execute the command with the given argument, expecting a return value
+                    value_after_execution = self.commands[command_name].execute(command_value, message)
+
+                    # if the command returns None, raise an error - this should never happen
+                    # since the command should always return a string
+                    if value_after_execution is None:
+                        raise ValueError(f"Command {command_name} returned None")
+
+                    # append the result of the command execution to the line results
+                    line_result.append(value_after_execution)
+                    i += 1
+
+                # if the part is plain text, just append it to the line results
+                elif classes_in_line[i][0] == "class:text":
+                    line_result.append(classes_in_line[i][1])
+                i += 1
+
+            # join all processed parts of the current line and add it to the lines list
+            lines.append("".join(line_result))
+
+        # join all processed lines into a single string with newline characters and return
+        return "\n".join(lines)
 
     def get_user_input(self) -> "UserInput":
         try:
             text = FormattedText([("#00AEAE", "G❯ ")])  # Define the prompt style and text.
-            message = self.prompt_session.prompt(text, validator=PromptValidator(), validate_while_typing=False)
+            message = self.main_prompt_session.prompt(text, validator=PromptValidator(), validate_while_typing=False)
             if message.strip() in ("exit", ":q"):
                 return UserInput(PromptAction.EXIT)
+
+            message = self.get_message_after_commands(message)
             return UserInput(PromptAction.CONTINUE, message)
         except (EOFError, KeyboardInterrupt):
             return UserInput(PromptAction.EXIT)
 
     def get_save_session_name(self) -> Optional[str]:
-        return self.prompt_session.prompt(
+        return self.text_prompt_session.prompt(
             "Enter a name to save this session under. A name will be generated for you if empty: ",
             validator=DummyValidator(),
-        )
+        ).strip(" ")
diff --git a/src/goose/cli/prompt/lexer.py b/src/goose/cli/prompt/lexer.py
index b21cae7ac..0e2bb0c91 100644
--- a/src/goose/cli/prompt/lexer.py
+++ b/src/goose/cli/prompt/lexer.py
@@ -5,6 +5,11 @@
 from prompt_toolkit.lexers import Lexer
 
 
+# These are lexers for the commands in the prompt. This is how we
+# are extracting the different parts of a command (here, used for styling),
+# but likely will be used to parse the command as well in the future.
+
+
 def completion_for_command(target_string: str) -> re.Pattern[str]:
     escaped_string = re.escape(target_string)
     vals = [f"(?:{escaped_string[:i]}(?=$))" for i in range(len(escaped_string), 0, -1)]
@@ -13,22 +18,21 @@ def completion_for_command(target_string: str) -> re.Pattern[str]:
 
 def command_itself(target_string: str) -> re.Pattern[str]:
     escaped_string = re.escape(target_string)
-    return re.compile(rf"(?<!\S)(\/{escaped_string})")
+    return re.compile(rf"(?<!\S)(\/{escaped_string}:?)")
 
 
 def value_for_command(command_string: str) -> re.Pattern[str]:
-    escaped_string = re.escape(command_string)
-    return re.compile(rf"(?<=(?<!\S)\/{escaped_string})([^\s]*)")
+    escaped_string = re.escape(command_string + ":")
+    return re.compile(rf"(?<=(?<!\S)\/{escaped_string})(?:(?:\"(.*?)(\"|$))|([^\s]*))")
 
 
 class PromptLexer(Lexer):
     def __init__(self, command_names: List[str]) -> None:
         self.patterns = []
         for command_name in command_names:
-            full_command = command_name + ":"
-            self.patterns.append((completion_for_command(full_command), "class:command"))
-            self.patterns.append((value_for_command(full_command), "class:parameter"))
-            self.patterns.append((command_itself(full_command), "class:command"))
+            self.patterns.append((completion_for_command(command_name), "class:command"))
+            self.patterns.append((value_for_command(command_name), "class:parameter"))
+            self.patterns.append((command_itself(command_name), "class:command"))
 
     def lex_document(self, document: Document) -> Callable[[int], list]:
         def get_line_tokens(line_number: int) -> Tuple[str, str]:
diff --git a/src/goose/cli/session.py b/src/goose/cli/session.py
index 4888e6154..1f72a3020 100644
--- a/src/goose/cli/session.py
+++ b/src/goose/cli/session.py
@@ -121,7 +121,7 @@ def __init__(
         if len(self.exchange.messages) == 0 and plan:
             self.setup_plan(plan=plan)
 
-        self.prompt_session = GoosePromptSession.create_prompt_session()
+        self.prompt_session = GoosePromptSession()
 
     def setup_plan(self, plan: dict) -> None:
         if len(self.exchange.messages):
diff --git a/src/goose/command/base.py b/src/goose/command/base.py
index dbf2d19db..2ed4ac2d0 100644
--- a/src/goose/command/base.py
+++ b/src/goose/command/base.py
@@ -8,9 +8,20 @@ class Command(ABC):
     """A command that can be executed by the CLI."""
 
     def get_completions(self, query: str) -> List[Completion]:
-        """Get completions for the command."""
+        """
+        Get completions for the command.
+
+        Args:
+            query (str): The current query.
+        """
         return []
 
-    def execute(self, query: str) -> Optional[str]:
-        """Execute's the command and replaces it with the output."""
+    def execute(self, query: str, surrounding_context: str) -> Optional[str]:
+        """
+        Execute's the command and replaces it with the output.
+
+        Args:
+            query (str): The query to execute.
+            surrounding_context (str): The full user message that the query is a part of.
+        """
         return ""
diff --git a/src/goose/command/file.py b/src/goose/command/file.py
index 7bbf7d9e3..95b10d53f 100644
--- a/src/goose/command/file.py
+++ b/src/goose/command/file.py
@@ -56,6 +56,5 @@ def get_completions(self, query: str) -> List[Completion]:
             )
         return completions
 
-    def execute(self, query: str) -> str | None:
-        # GOOSE-TODO: return the query
-        pass
+    def execute(self, query: str, _: str) -> str | None:
+        return query
diff --git a/tests/cli/prompt/test_goose_prompt_session.py b/tests/cli/prompt/test_goose_prompt_session.py
index eca44cc67..1c9578fa2 100644
--- a/tests/cli/prompt/test_goose_prompt_session.py
+++ b/tests/cli/prompt/test_goose_prompt_session.py
@@ -1,5 +1,6 @@
 from unittest.mock import patch
 
+from prompt_toolkit import PromptSession
 import pytest
 from goose.cli.prompt.goose_prompt_session import GoosePromptSession
 from goose.cli.prompt.user_input import PromptAction, UserInput
@@ -7,41 +8,48 @@
 
 @pytest.fixture
 def mock_prompt_session():
-    with patch("prompt_toolkit.PromptSession") as mock_prompt_session:
+    with patch("goose.cli.prompt.goose_prompt_session.PromptSession") as mock_prompt_session:
         yield mock_prompt_session
 
 
 def test_get_save_session_name(mock_prompt_session):
-    mock_prompt_session.prompt.return_value = "my_session"
-    goose_prompt_session = GoosePromptSession(mock_prompt_session)
+    mock_prompt_session.return_value.prompt.return_value = "my_session"
+    goose_prompt_session = GoosePromptSession()
 
     assert goose_prompt_session.get_save_session_name() == "my_session"
 
 
-def test_get_user_input_to_continue(mock_prompt_session):
-    mock_prompt_session.prompt.return_value = "input_value"
-    goose_prompt_session = GoosePromptSession(mock_prompt_session)
+def test_get_save_session_name_with_space(mock_prompt_session):
+    mock_prompt_session.return_value.prompt.return_value = "my_session "
+    goose_prompt_session = GoosePromptSession()
 
-    user_input = goose_prompt_session.get_user_input()
+    assert goose_prompt_session.get_save_session_name() == "my_session"
+
+
+def test_get_user_input_to_continue():
+    with patch.object(PromptSession, "prompt", return_value="input_value"):
+        goose_prompt_session = GoosePromptSession()
+
+        user_input = goose_prompt_session.get_user_input()
 
-    assert user_input == UserInput(PromptAction.CONTINUE, "input_value")
+        assert user_input == UserInput(PromptAction.CONTINUE, "input_value")
 
 
 @pytest.mark.parametrize("exit_input", ["exit", ":q"])
 def test_get_user_input_to_exit(exit_input, mock_prompt_session):
-    mock_prompt_session.prompt.return_value = exit_input
-    goose_prompt_session = GoosePromptSession(mock_prompt_session)
+    with patch.object(PromptSession, "prompt", return_value=exit_input):
+        goose_prompt_session = GoosePromptSession()
 
-    user_input = goose_prompt_session.get_user_input()
+        user_input = goose_prompt_session.get_user_input()
 
-    assert user_input == UserInput(PromptAction.EXIT)
+        assert user_input == UserInput(PromptAction.EXIT)
 
 
 @pytest.mark.parametrize("error", [EOFError, KeyboardInterrupt])
 def test_get_user_input_to_exit_when_error_occurs(error, mock_prompt_session):
-    mock_prompt_session.prompt.side_effect = error
-    goose_prompt_session = GoosePromptSession(mock_prompt_session)
+    with patch.object(PromptSession, "prompt", side_effect=error):
+        goose_prompt_session = GoosePromptSession()
 
-    user_input = goose_prompt_session.get_user_input()
+        user_input = goose_prompt_session.get_user_input()
 
-    assert user_input == UserInput(PromptAction.EXIT)
+        assert user_input == UserInput(PromptAction.EXIT)
diff --git a/tests/cli/prompt/test_lexer.py b/tests/cli/prompt/test_lexer.py
index 585bead9b..790bed40b 100644
--- a/tests/cli/prompt/test_lexer.py
+++ b/tests/cli/prompt/test_lexer.py
@@ -232,22 +232,45 @@ def test_lex_document_ending_char_of_parameter_is_symbol():
     assert actual_tokens == expected_tokens
 
 
-def test_command_itself():
-    pattern = command_itself("file:")
-    matches = pattern.match("/file:example.txt")
+def assert_pattern_matches(pattern, text, expected_group):
+    matches = pattern.search(text)
     assert matches is not None
-    assert matches.group(1) == "/file:"
+    assert matches.group() == expected_group
+
+
+def test_command_itself():
+    pattern = command_itself("file")
+    assert_pattern_matches(pattern, "/file:example.txt", "/file:")
+    assert_pattern_matches(pattern, "/file asdf", "/file")
+    assert_pattern_matches(pattern, "some /file", "/file")
+    assert_pattern_matches(pattern, "some /file:", "/file:")
+    assert_pattern_matches(pattern, "/file /file", "/file")
+
+    assert pattern.search("file") is None
+    assert pattern.search("/anothercommand") is None
 
 
 def test_value_for_command():
-    pattern = value_for_command("file:")
-    matches = pattern.search("/file:example.txt")
-    assert matches is not None
-    assert matches.group(1) == "example.txt"
+    pattern = value_for_command("file")
+    assert_pattern_matches(pattern, "/file:example.txt", "example.txt")
+    assert_pattern_matches(pattern, '/file:"example space.txt"', '"example space.txt"')
+    assert_pattern_matches(pattern, '/file:"example.txt" some other string', '"example.txt"')
+    assert_pattern_matches(pattern, "something before /file:example.txt", "example.txt")
+
+    # assert no pattern matches when there is no value
+    assert pattern.search("/file:").group() == ""
+    assert pattern.search("/file: other").group() == ""
+    assert pattern.search("/file: ").group() == ""
+    assert pattern.search("/file other") is None
 
 
 def test_completion_for_command():
-    pattern = completion_for_command("file:")
-    matches = pattern.search("/file:")
-    assert matches is not None
-    assert matches.group(1) == "file:"
+    pattern = completion_for_command("file")
+    assert_pattern_matches(pattern, "/file", "/file")
+    assert_pattern_matches(pattern, "/fi", "/fi")
+    assert_pattern_matches(pattern, "before /fi", "/fi")
+    assert_pattern_matches(pattern, "some /f", "/f")
+
+    assert pattern.search("/file after") is None
+    assert pattern.search("/ file") is None
+    assert pattern.search("/file:") is None