diff --git a/.gitignore b/.gitignore
index 5b41b0b2d..b1f355448 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,6 +1,4 @@
-image.*
-video.mp4
-video.webm
+# Python, Flask, IDEs
 cache/
 __pycache__/
 .idea/
@@ -12,3 +10,11 @@ flask_session/
 .DS_Store
 .venv
 *.pyc
+
+# rdrama Media Runtime Artifacts
+image.*
+video.mp4
+video.webm
+
+# Optional env file for some environments
+env
diff --git a/files/__main__.py b/files/__main__.py
index 7828f30ec..f0e1a3be2 100644
--- a/files/__main__.py
+++ b/files/__main__.py
@@ -50,7 +50,8 @@ if bool_from_string(environ.get("ENFORCE_PRODUCTION", True)) and app.debug:
 
 if environ.get("SITE_ID") is None:
 	from dotenv import load_dotenv
-	load_dotenv(dotenv_path=Path("env"))
+	load_dotenv(dotenv_path=Path("bootstrap/site_env"))
+	load_dotenv(dotenv_path=Path("env"), override=True)
 
 # ...and let's add the flask profiler if it's enabled...
 
diff --git a/poetry.lock b/poetry.lock
index f693f5ee9..b6de3c2d7 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -718,6 +718,17 @@ python-versions = "!=3.0.*,!=3.1.*,!=3.2.*,>=2.7"
 [package.dependencies]
 six = ">=1.5"
 
+[[package]]
+name = "python-dotenv"
+version = "1.0.0"
+description = "Read key-value pairs from a .env file and set them as environment variables"
+category = "main"
+optional = false
+python-versions = ">=3.8"
+
+[package.extras]
+cli = ["click (>=5.0)"]
+
 [[package]]
 name = "python-engineio"
 version = "4.3.4"
@@ -1065,7 +1076,7 @@ testing = ["coverage (>=5.0.3)", "zope.event", "zope.testing"]
 [metadata]
 lock-version = "1.1"
 python-versions = "~3.10"    # updating to 3.11 causes instability; see https://github.com/themotte/rDrama/issues/446
-content-hash = "bb33c14d0075dd9f0d81589e0445495444bfe16c73bd9cd9f88e3d17e60cab0e"
+content-hash = "0607803380bd7078b955572621d5f794e7eeb3fa08a5794c17fac0e14e980431"
 
 [metadata.files]
 alembic = [
@@ -1997,6 +2008,10 @@ python-dateutil = [
     {file = "python-dateutil-2.8.2.tar.gz", hash = "sha256:0123cacc1627ae19ddf3c27a5de5bd67ee4586fbdd6440d9748f8abb483d3e86"},
     {file = "python_dateutil-2.8.2-py2.py3-none-any.whl", hash = "sha256:961d03dc3453ebbc59dbdea9e4e11c5651520a876d0f4db161e8674aae935da9"},
 ]
+python-dotenv = [
+    {file = "python-dotenv-1.0.0.tar.gz", hash = "sha256:a8df96034aae6d2d50a4ebe8216326c61c3eb64836776504fcca410e5937a3ba"},
+    {file = "python_dotenv-1.0.0-py3-none-any.whl", hash = "sha256:f5971a9226b701070a4bf2c38c89e5a3f0d64de8debda981d1db98583009122a"},
+]
 python-engineio = [
     {file = "python-engineio-4.3.4.tar.gz", hash = "sha256:d8d8b072799c36cadcdcc2b40d2a560ce09797ab3d2d596b2ad519a5e4df19ae"},
     {file = "python_engineio-4.3.4-py3-none-any.whl", hash = "sha256:7454314a529bba20e745928601ffeaf101c1b5aca9a6c4e48ad397803d10ea0c"},
diff --git a/pyproject.toml b/pyproject.toml
index 21c87d01f..f00c8a269 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -27,6 +27,7 @@ matplotlib = "*"
 Pillow = "*"
 psutil = "*"
 pyotp = "*"
+python-dotenv = "*"
 qrcode = "*"
 redis = "*"
 requests = "*"