diff --git a/towncrier/newsfragments/2207.bugfix b/towncrier/newsfragments/2207.bugfix
new file mode 100644
index 00000000..f448f174
--- /dev/null
+++ b/towncrier/newsfragments/2207.bugfix
@@ -0,0 +1 @@
+Will update /etc/nginx/nginx.conf and /etc/nginx/http.d/rainloop.conf in webmail container to support MESSAGE_SIZE_LIMIT
\ No newline at end of file
diff --git a/webmails/rainloop/Dockerfile b/webmails/rainloop/Dockerfile
index 8f77ab5c..fd4b7549 100644
--- a/webmails/rainloop/Dockerfile
+++ b/webmails/rainloop/Dockerfile
@@ -36,10 +36,11 @@ RUN apk add --no-cache \
  && rm /etc/nginx/http.d/default.conf \
  && rm /etc/php7/php-fpm.d/www.conf \
  && mkdir -p /run/nginx \
- && mkdir -p /var/www/rainloop
+ && mkdir -p /var/www/rainloop \
+ && mkdir -p /config
 
 # nginx / PHP config files
-COPY config/nginx-rainloop.conf /etc/nginx/http.d/rainloop.conf
+COPY config/nginx-rainloop.conf /config/nginx-rainloop.conf
 COPY config/php-rainloop.conf /etc/php7/php-fpm.d/rainloop.conf
 
 # Rainloop login
@@ -67,11 +68,12 @@ RUN apk add --no-cache \
  && apk del unzip
 
 COPY start.py /start.py
+COPY config.py /config.py
 
 EXPOSE 80/tcp
 VOLUME ["/data"]
 
-CMD php-fpm7 && /start.py
+CMD /start.py
 
 HEALTHCHECK CMD curl -f -L http://localhost/ || exit 1
 RUN echo $VERSION >> /version
diff --git a/webmails/rainloop/config.py b/webmails/rainloop/config.py
new file mode 100755
index 00000000..88052961
--- /dev/null
+++ b/webmails/rainloop/config.py
@@ -0,0 +1,15 @@
+#!/usr/bin/python3
+
+import os
+import logging as log
+import sys
+from socrate import system, conf
+
+args = os.environ.copy()
+
+log.basicConfig(stream=sys.stderr, level=args.get("LOG_LEVEL", "WARNING"))
+
+# Build final configuration paths
+conf.jinja("/config/nginx-rainloop.conf", args, "/etc/nginx/http.d/rainloop.conf")
+if os.path.exists("/var/run/nginx.pid"):
+    os.system("nginx -s reload")
diff --git a/webmails/rainloop/config/nginx-rainloop.conf b/webmails/rainloop/config/nginx-rainloop.conf
index dfdbf8f7..be40e963 100644
--- a/webmails/rainloop/config/nginx-rainloop.conf
+++ b/webmails/rainloop/config/nginx-rainloop.conf
@@ -3,7 +3,7 @@ server {
     listen [::]:80 default_server;
 
     root /var/www/rainloop;
-    
+
     # /dev/stdout (Default), <path>, off
     access_log off;
 
@@ -12,13 +12,16 @@ server {
 
     index index.php;
 
+    # set maximum body size to configured limit
+    client_max_body_size {{ MESSAGE_SIZE_LIMIT|int + 8388608 }};
+
     location / {
         try_files $uri /index.php?$query_string;
     }
 
     location ~ \.php$ {
         fastcgi_split_path_info ^(.+\.php)(/.*)$;
-        
+
         fastcgi_intercept_errors on;
         fastcgi_index  index.php;
 
diff --git a/webmails/rainloop/start.py b/webmails/rainloop/start.py
index a52b70e9..3905791f 100755
--- a/webmails/rainloop/start.py
+++ b/webmails/rainloop/start.py
@@ -4,6 +4,7 @@ import os
 import shutil
 import logging as log
 import sys
+import subprocess
 from socrate import system, conf
 
 log.basicConfig(stream=sys.stderr, level=os.environ.get("LOG_LEVEL", "WARNING"))
@@ -22,8 +23,11 @@ os.makedirs(base + "configs", exist_ok=True)
 conf.jinja("/defaults/default.ini", os.environ, "/data/_data_/_default_/domains/default.ini")
 conf.jinja("/defaults/application.ini", os.environ, "/data/_data_/_default_/configs/application.ini")
 conf.jinja("/defaults/php.ini", os.environ, "/etc/php7/php.ini")
+# Start the fastcgi process manager now that config files have been adjusted
+os.system("php-fpm7")
 
 os.system("chown -R nginx:nginx /data")
 os.system("chmod -R a+rX /var/www/rainloop/")
 
+subprocess.call(["/config.py"])
 os.execv("/usr/sbin/nginx", ["nginx", "-g", "daemon off;"])