diff --git a/run.py b/run.py
new file mode 100644
index 0000000..f2ce820
--- /dev/null
+++ b/run.py
@@ -0,0 +1,135 @@
+#!/usr/bin/python3
+from __future__ import annotations
+
+import tomllib
+from dataclasses import dataclass
+from functools import cached_property
+from os import name as os_name, system as cmd
+from pathlib import Path
+from typing import TYPE_CHECKING
+
+if TYPE_CHECKING:
+    from chalky import Chalk
+
+ROOT = Path(__file__).parent
+IS_WIN = os_name == "nt"
+QUIET_SUFFIX = " > NUL" if IS_WIN else " > /dev/null"
+OS_KEY = "windows" if IS_WIN else "linux"
+
+
+class Sources:
+    def __init__(self) -> None:
+        self.__src_dir = ROOT / "src"
+
+    @cached_property
+    def languages(self) -> dict[str, Language]:
+        languages = {}
+
+        for language_dir in self.__src_dir.iterdir():
+            if not language_dir.is_dir():
+                continue
+
+            language_metadata = tomllib.loads((language_dir / "language.toml").read_text())
+            language_metadata["directory"] = language_dir
+
+            language = Language.from_raw(language_metadata)
+
+            languages[language.name] = language
+
+        return languages
+
+
+@dataclass
+class Colors:
+    fg: Chalk
+    bg: Chalk
+
+
+class Language:
+    def __init__(
+        self,
+        *,
+        directory: Path,
+        name: str,
+        description: str,
+        colors: Colors,
+        build_command: str | None,
+        run_command: str,
+    ) -> None:
+        self.__directory = directory
+
+        self.name = name
+        self.description = description
+        self.colors = colors
+        self.build_command = build_command
+        self.run_command = run_command
+
+    @classmethod
+    def from_raw(cls, raw: dict) -> Language:
+        colors = raw["colors"]
+
+        build = raw.get("build", {})
+        run = raw["run"]
+        return cls(
+            directory=raw["directory"],
+
+            name=raw["name"],
+            description=raw["description"],
+            colors=Colors(
+                fg=colors["foreground"],
+                bg=colors["background"],
+            ),
+            build_command=build.get("common", build.get(OS_KEY)),
+            run_command=run.get("common", run.get(OS_KEY)),
+        )
+
+    @property
+    def assignments(self) -> dict[str, Assignment]:
+        for assignment_dir in self.__directory.iterdir():
+            if not assignment_dir.is_dir():
+                continue
+
+            assignment_metadata = tomllib.loads((assignment_dir / "assignment.toml").read_text())
+            assignment_metadata["directory"] = assignment_dir
+            assignment_metadata["language"] = self
+
+            yield Assignment.from_raw(assignment_metadata)
+
+
+class Assignment:
+    def __init__(
+        self,
+        *,
+        language: Language,
+        directory: Path,
+        name: str,
+        date: str,
+        description: str,
+        directions: str,
+    ) -> None:
+        self.language = language
+        self.__directory = directory
+
+        self.name = name
+        self.date = date
+        self.description = description
+        self.directions = directions
+
+    @classmethod
+    def from_raw(cls, raw: dict) -> Assignment:
+        return cls(
+            language=raw["language"],
+            directory=raw["directory"],
+
+            name=raw["name"],
+            date=raw["date"],
+            description=raw["description"],
+            directions=raw["directions"],
+        )
+
+    def compile(self, *, quiet: bool = False) -> bool | None:
+        """None = not a compiled language"""
+        if self.language.build_command is None:
+            return None
+
+        return cmd(self.language.build_command + (QUIET_SUFFIX if quiet else "")) == 0
diff --git a/sources/c/example/assignment.toml b/sources/c/example/assignment.toml
new file mode 100644
index 0000000..39acc28
--- /dev/null
+++ b/sources/c/example/assignment.toml
@@ -0,0 +1,9 @@
+name = "example"
+given-date = "3/11/2022"
+description = "This is an example entry for C"
+directions = """
+Print "Example" 10 times.
+"""
+
+[compile]
+main-file = "example.c"
diff --git a/sources/c/example/example.c b/sources/c/example/example.c
new file mode 100644
index 0000000..238dfb0
--- /dev/null
+++ b/sources/c/example/example.c
@@ -0,0 +1,8 @@
+#include <stdio.h>
+
+int main() {
+    for (int i = 0; i < 10; i++) {
+        printf("Example");
+    }
+    return 0;
+}
diff --git a/sources/c/language.toml b/sources/c/language.toml
new file mode 100644
index 0000000..399cf37
--- /dev/null
+++ b/sources/c/language.toml
@@ -0,0 +1,16 @@
+name = "C"
+description = "C (pronounced like the letter c) is a general-purpose computer programming language"
+
+[colors]
+foreground = 0x000000
+background = 0x00599d
+
+[build]
+common = "gcc -o {out-file} {main-file}"
+
+[run]
+linux = "./{out-file}"
+windows = "{out-file}"
+
+[dependencies]
+common = ["gcc"]
diff --git a/src/C/star-rating:30.11.2022/ASSIGNMENT b/sources/c/star-rating/assignment.toml
similarity index 76%
rename from src/C/star-rating:30.11.2022/ASSIGNMENT
rename to sources/c/star-rating/assignment.toml
index d159ff0..87dbd88 100644
--- a/src/C/star-rating:30.11.2022/ASSIGNMENT
+++ b/sources/c/star-rating/assignment.toml
@@ -1,3 +1,7 @@
+name = "star-rating"
+given-date = "30/10/2022"
+description = "A program that takes 21 reviews and calculates the average rating and prints some stars"
+directions = """
 1. Read in 21 user ratings for a movie.
 Each rating is a number from 1 to 5 stars.
 Store the ratings in an array.
@@ -20,4 +24,8 @@ number. See screenshot.
 contains the percentage of ratings for each
 star, e.g. 14.3% one star, 23.8% two star, etc.
 Display this to the screen in a similar manner
-to task 4.
\ No newline at end of file
+to task 4.
+"""
+
+[compile]
+main-file = "star_rating.c"
diff --git a/src/C/star-rating:30.11.2022/star_rating.c b/sources/c/star-rating/star_rating.c
similarity index 100%
rename from src/C/star-rating:30.11.2022/star_rating.c
rename to sources/c/star-rating/star_rating.c
diff --git a/sources/cpython/example/assignment.toml b/sources/cpython/example/assignment.toml
new file mode 100644
index 0000000..6c9fd3a
--- /dev/null
+++ b/sources/cpython/example/assignment.toml
@@ -0,0 +1,9 @@
+name = "example"
+given-date = "3/11/2022"
+description = "This is an example entry for CPython"
+directions = """
+Print "Example" 10 times.
+"""
+
+[compile]
+main-file = "example.py"
diff --git a/sources/cpython/example/example.py b/sources/cpython/example/example.py
new file mode 100644
index 0000000..e84bf70
--- /dev/null
+++ b/sources/cpython/example/example.py
@@ -0,0 +1,2 @@
+for _ in range(10):
+    print("Example")
diff --git a/sources/cpython/language.toml b/sources/cpython/language.toml
new file mode 100644
index 0000000..79f328f
--- /dev/null
+++ b/sources/cpython/language.toml
@@ -0,0 +1,14 @@
+name = "CPython"
+description = "Python is a high-level, general-purpose programming language"
+
+[colors]
+foreground = 0xfed140
+background = 0x3670a0
+
+[run]
+linux = "python3 {main-file}"
+windows = "py {main-file}"
+
+[dependencies]
+linux = ["python3"]
+windows = ["py"]
diff --git a/src/C/BGCOLOR b/src/C/BGCOLOR
deleted file mode 100644
index a66fa0d..0000000
--- a/src/C/BGCOLOR
+++ /dev/null
@@ -1 +0,0 @@
-00599d
\ No newline at end of file
diff --git a/src/C/COMPILECMD b/src/C/COMPILECMD
deleted file mode 100644
index c3cba06..0000000
--- a/src/C/COMPILECMD
+++ /dev/null
@@ -1 +0,0 @@
-gcc -o {out} {main}
\ No newline at end of file
diff --git a/src/C/DESCRIPTION b/src/C/DESCRIPTION
deleted file mode 100644
index b754c14..0000000
--- a/src/C/DESCRIPTION
+++ /dev/null
@@ -1 +0,0 @@
-C (pronounced like the letter c) is a general-purpose computer programming language
\ No newline at end of file
diff --git a/src/C/FGCOLOR b/src/C/FGCOLOR
deleted file mode 100644
index de53aff..0000000
--- a/src/C/FGCOLOR
+++ /dev/null
@@ -1 +0,0 @@
-ffffff
\ No newline at end of file
diff --git a/src/C/star-rating:30.11.2022/DESCRIPTION b/src/C/star-rating:30.11.2022/DESCRIPTION
deleted file mode 100644
index dcca539..0000000
--- a/src/C/star-rating:30.11.2022/DESCRIPTION
+++ /dev/null
@@ -1 +0,0 @@
-Does stuff with reviews TODO do desc
\ No newline at end of file
diff --git a/src/C/star-rating:30.11.2022/MAIN b/src/C/star-rating:30.11.2022/MAIN
deleted file mode 100644
index 52efa0a..0000000
--- a/src/C/star-rating:30.11.2022/MAIN
+++ /dev/null
@@ -1 +0,0 @@
-star_rating.c
\ No newline at end of file
diff --git a/src/CPython/BGCOLOR b/src/CPython/BGCOLOR
deleted file mode 100644
index 7761eea..0000000
--- a/src/CPython/BGCOLOR
+++ /dev/null
@@ -1 +0,0 @@
-3670a0
\ No newline at end of file
diff --git a/src/CPython/DESCRIPTION b/src/CPython/DESCRIPTION
deleted file mode 100644
index 73ec8b8..0000000
--- a/src/CPython/DESCRIPTION
+++ /dev/null
@@ -1 +0,0 @@
-Python is a high-level, general-purpose programming language
\ No newline at end of file
diff --git a/src/CPython/FGCOLOR b/src/CPython/FGCOLOR
deleted file mode 100644
index 8f1bb31..0000000
--- a/src/CPython/FGCOLOR
+++ /dev/null
@@ -1 +0,0 @@
-fed140
\ No newline at end of file
diff --git a/src/CPython/RUNCMD b/src/CPython/RUNCMD
deleted file mode 100644
index c4a3c0b..0000000
--- a/src/CPython/RUNCMD
+++ /dev/null
@@ -1 +0,0 @@
-python3 {main}
\ No newline at end of file
diff --git a/src/CPython/test:1.1.1/ASSIGNMENT b/src/CPython/test:1.1.1/ASSIGNMENT
deleted file mode 100644
index 4bad556..0000000
--- a/src/CPython/test:1.1.1/ASSIGNMENT
+++ /dev/null
@@ -1 +0,0 @@
-test directions
\ No newline at end of file
diff --git a/src/CPython/test:1.1.1/DESCRIPTION b/src/CPython/test:1.1.1/DESCRIPTION
deleted file mode 100644
index 1b12b17..0000000
--- a/src/CPython/test:1.1.1/DESCRIPTION
+++ /dev/null
@@ -1 +0,0 @@
-test desc
\ No newline at end of file
diff --git a/src/CPython/test:1.1.1/MAIN b/src/CPython/test:1.1.1/MAIN
deleted file mode 100644
index 9465664..0000000
--- a/src/CPython/test:1.1.1/MAIN
+++ /dev/null
@@ -1 +0,0 @@
-test.py
\ No newline at end of file
diff --git a/src/CPython/test:1.1.1/test.py b/src/CPython/test:1.1.1/test.py
deleted file mode 100644
index 03797e7..0000000
--- a/src/CPython/test:1.1.1/test.py
+++ /dev/null
@@ -1 +0,0 @@
-print("test print")