diff --git a/app/client/Dockerfile b/app/client/Dockerfile
index ad7ac70c36..6e82c14688 100644
--- a/app/client/Dockerfile
+++ b/app/client/Dockerfile
@@ -5,7 +5,7 @@ COPY ./build /var/www/appsmith
 EXPOSE 80
 # This is the default nginx template file inside the container. 
 # This is replaced by the install.sh script during a deployment
-COPY ./docker/templates/nginx-linux.conf.template /nginx.conf.template
+COPY ./docker/templates/nginx-app.conf.template /nginx.conf.template
 COPY ./docker/templates/nginx-root.conf.template /nginx-root.conf.template
 # This is the script that is used to start Nginx when the Docker container starts
 COPY ./docker/start-nginx.sh /start-nginx.sh
diff --git a/app/client/cypress/setup-test.sh b/app/client/cypress/setup-test.sh
index 944f88aa74..22241bfe14 100755
--- a/app/client/cypress/setup-test.sh
+++ b/app/client/cypress/setup-test.sh
@@ -10,7 +10,7 @@ serve -s build -p 3000 &
 
 # Substitute all the env variables in nginx
 vars_to_substitute=$(printf '\$%s,' $(env | grep -o "^APPSMITH_[A-Z0-9_]\+" | xargs))
-cat ./docker/templates/nginx-linux.conf.template | envsubst ${vars_to_substitute} | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > ./docker/nginx.conf
+cat ./docker/templates/nginx-app.conf.template | sed -e "s|__APPSMITH_CLIENT_PROXY_PASS__|http://localhost:3000|g" | sed -e "s|__APPSMITH_SERVER_PROXY_PASS__|http://localhost:8080|g" | envsubst ${vars_to_substitute} | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > ./docker/nginx.conf
 cat ./docker/templates/nginx-root.conf.template | envsubst ${vars_to_substitute} | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > ./docker/nginx-root.conf
 
 # Create the SSL files for Nginx. Required for service workers to work properly.
diff --git a/app/client/docker/start-nginx.sh b/app/client/docker/start-nginx.sh
index 17e69a3dac..cf29bb7e3a 100755
--- a/app/client/docker/start-nginx.sh
+++ b/app/client/docker/start-nginx.sh
@@ -2,6 +2,6 @@
 # This script is baked into the appsmith-editor Dockerfile and is used to boot Nginx when the Docker container starts
 # Refer: /app/client/Dockerfile
 set -ue
-cat /nginx.conf.template | envsubst "$(printf '$%s,' $(env | grep -Eo '^APPSMITH_[A-Z0-9_]+'))" | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > /etc/nginx/conf.d/default.conf
+cat /nginx.conf.template | sed -e "s|__APPSMITH_CLIENT_PROXY_PASS__|http://localhost:3000|g" | sed -e "s|__APPSMITH_SERVER_PROXY_PASS__|http://localhost:8080|g" | envsubst "$(printf '$%s,' $(env | grep -Eo '^APPSMITH_[A-Z0-9_]+'))" | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > /etc/nginx/conf.d/default.conf
 cat /nginx-root.conf.template | envsubst "$(printf '$%s,' $(env | grep -Eo '^APPSMITH_[A-Z0-9_]+'))" | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > /etc/nginx/nginx.conf
 exec nginx -g 'daemon off;'
diff --git a/app/client/docker/templates/nginx-linux.conf.template b/app/client/docker/templates/nginx-app.conf.template
similarity index 93%
rename from app/client/docker/templates/nginx-linux.conf.template
rename to app/client/docker/templates/nginx-app.conf.template
index 2aff04381c..b7cb502f93 100644
--- a/app/client/docker/templates/nginx-linux.conf.template
+++ b/app/client/docker/templates/nginx-app.conf.template
@@ -24,10 +24,9 @@ server {
     proxy_set_header X-Forwarded-Host $host;
     proxy_set_header Accept-Encoding "";
 
-
     sub_filter_once off;
     location / {
-        proxy_pass http://localhost:3000;
+        proxy_pass __APPSMITH_CLIENT_PROXY_PASS__;
         sub_filter __APPSMITH_SENTRY_DSN__ '${APPSMITH_SENTRY_DSN}';
         sub_filter __APPSMITH_SMART_LOOK_ID__ '${APPSMITH_SMART_LOOK_ID}';
         sub_filter __APPSMITH_OAUTH2_GOOGLE_CLIENT_ID__ '${APPSMITH_OAUTH2_GOOGLE_CLIENT_ID}';
@@ -57,19 +56,19 @@ server {
     location /api {
         proxy_set_header X-Forwarded-Proto $scheme;
         proxy_set_header X-Forwarded-Host $host;
-        proxy_pass http://localhost:8080;
+        proxy_pass __APPSMITH_SERVER_PROXY_PASS__;
     }
 
     location /oauth2 {
         proxy_set_header X-Forwarded-Proto $scheme;
         proxy_set_header X-Forwarded-Host $host;
-        proxy_pass http://localhost:8080;
+        proxy_pass __APPSMITH_SERVER_PROXY_PASS__;
     }
 
     location /login {
         proxy_set_header X-Forwarded-Proto $scheme;
         proxy_set_header X-Forwarded-Host $host;
-        proxy_pass http://localhost:8080;
+        proxy_pass __APPSMITH_SERVER_PROXY_PASS__;
     }
 }
 
diff --git a/app/client/docker/templates/nginx-mac.conf.template b/app/client/docker/templates/nginx-mac.conf.template
deleted file mode 100644
index 0ae113a45e..0000000000
--- a/app/client/docker/templates/nginx-mac.conf.template
+++ /dev/null
@@ -1,76 +0,0 @@
-server {
-    listen 80;
-    server_name dev.appsmith.com;
-
-    return 301 https://$host$request_uri;
-}
-
-server {
-    listen 443 ssl http2;
-    server_name dev.appsmith.com;
-    client_max_body_size 10m;
-
-    ssl_certificate /etc/certificate/dev.appsmith.com.pem;
-    ssl_certificate_key /etc/certificate/dev.appsmith.com-key.pem;
-
-    # include /etc/letsencrypt/options-ssl-nginx.conf;
-    # ssl_dhparam /etc/letsencrypt/ssl-dhparams.pem;
-    gzip on;
-
-    proxy_ssl_server_name on;
-    proxy_set_header Upgrade $http_upgrade;
-    proxy_set_header Connection "upgrade";
-    proxy_set_header Accept-Encoding "";
-
-    index index.html index.htm;
-
-    sub_filter_once off;
-    location / {
-        proxy_pass http://host.docker.internal:3000;
-        sub_filter __APPSMITH_SENTRY_DSN__ '${APPSMITH_SENTRY_DSN}';
-        sub_filter __APPSMITH_SMART_LOOK_ID__ '${APPSMITH_SMART_LOOK_ID}';
-        sub_filter __APPSMITH_OAUTH2_GOOGLE_CLIENT_ID__ '${APPSMITH_OAUTH2_GOOGLE_CLIENT_ID}';
-        sub_filter __APPSMITH_OAUTH2_GITHUB_CLIENT_ID__ '${APPSMITH_OAUTH2_GITHUB_CLIENT_ID}';
-        sub_filter __APPSMITH_MARKETPLACE_ENABLED__ '${APPSMITH_MARKETPLACE_ENABLED}';
-        sub_filter __APPSMITH_SEGMENT_KEY__ '${APPSMITH_SEGMENT_KEY}';
-        sub_filter __APPSMITH_OPTIMIZELY_KEY__ '${APPSMITH_OPTIMIZELY_KEY}';
-        sub_filter __APPSMITH_ALGOLIA_API_ID__ '${APPSMITH_ALGOLIA_API_ID}';
-        sub_filter __APPSMITH_ALGOLIA_SEARCH_INDEX_NAME__ '${APPSMITH_ALGOLIA_SEARCH_INDEX_NAME}';
-        sub_filter __APPSMITH_ALGOLIA_API_KEY__ '${APPSMITH_ALGOLIA_API_KEY}';
-        sub_filter __APPSMITH_CLIENT_LOG_LEVEL__ '${APPSMITH_CLIENT_LOG_LEVEL}';
-        sub_filter __APPSMITH_GOOGLE_MAPS_API_KEY__ '${APPSMITH_GOOGLE_MAPS_API_KEY}';
-        sub_filter __APPSMITH_TNC_PP__ '${APPSMITH_TNC_PP}';
-        sub_filter __APPSMITH_SENTRY_RELEASE__ '${APPSMITH_SENTRY_RELEASE}';
-        sub_filter __APPSMITH_SENTRY_ENVIRONMENT__ '${APPSMITH_SENTRY_ENVIRONMENT}';
-        sub_filter __APPSMITH_VERSION_ID__ '${APPSMITH_VERSION_ID}';
-        sub_filter __APPSMITH_VERSION_RELEASE_DATE__ '${APPSMITH_VERSION_RELEASE_DATE}';
-        sub_filter __APPSMITH_INTERCOM_APP_ID__ '${APPSMITH_INTERCOM_APP_ID}';
-        sub_filter __APPSMITH_MAIL_ENABLED__ '${APPSMITH_MAIL_ENABLED}';
-        sub_filter __APPSMITH_DISABLE_TELEMETRY__ '${APPSMITH_DISABLE_TELEMETRY}';
-    }
-
-
-    location /f {
-       proxy_pass https://cdn.optimizely.com/;
-    }
-
-    location /api {
-        proxy_set_header X-Forwarded-Proto $scheme;
-        proxy_set_header X-Forwarded-Host $host;
-        proxy_pass http://host.docker.internal:8080;
-    }
-
-    location /oauth2 {
-        proxy_set_header X-Forwarded-Proto $scheme;
-        proxy_set_header X-Forwarded-Host $host;
-
-        proxy_pass http://host.docker.internal:8080;
-    }
-
-    location /login {
-        proxy_set_header X-Forwarded-Proto $scheme;
-        proxy_set_header X-Forwarded-Host $host;
-
-        proxy_pass http://host.docker.internal:8080;
-    }
-}
diff --git a/app/client/start-https.sh b/app/client/start-https.sh
index f28eaacc63..98d9e0cbee 100755
--- a/app/client/start-https.sh
+++ b/app/client/start-https.sh
@@ -43,16 +43,41 @@ else
     export $(grep -v '^[[:space:]]*#' ${ENV_FILE} | xargs)
 fi
 
-unameOut="$(uname -s)"
+# Stop and remove existing container
+# Ignore outcome in case someone decides to set -e later
+docker rm -f wildcard-nginx || true
+
+
+default_server_proxy="http://host.docker.internal:8080"
+default_client_proxy="http://host.docker.internal:3000"
+
+default_linux_server_proxy="http://localhost:8080"
+default_linux_client_proxy="http://localhost:3000"
+
+# default server to internal docker
+server_proxy_pass="${1:-$default_server_proxy}"
+
+uname_out="$(uname -s)"
 vars_to_substitute="$(printf '\$%s,' $(grep -o "^APPSMITH_[A-Z0-9_]\+" ../../.env | xargs))"
-case "${unameOut}" in
+client_proxy_pass="${default_client_proxy}"
+network_mode="bridge"
+case "${uname_out}" in
     Linux*)     machine=Linux
+        # If we're not in WSL, use the mode that works
+        if [[ "$(< /proc/version)" != *@(icrosoft|WSL)* ]]; then
+	        network_mode="host"
+	        client_proxy_pass=$default_linux_client_proxy
+            # if no server was passed
+            if [[ -z $1 ]]; then
+                server_proxy_pass=$default_linux_server_proxy
+            fi
+        fi
                 echo "
     Starting nginx for Linux...
     "
-                cat ./docker/templates/nginx-linux.conf.template | envsubst ${vars_to_substitute} | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > ./docker/nginx.conf  &&
+                cat ./docker/templates/nginx-app.conf.template | sed -e "s|__APPSMITH_CLIENT_PROXY_PASS__|${client_proxy_pass}|g" | sed -e "s|__APPSMITH_SERVER_PROXY_PASS__|${server_proxy_pass}|g" | envsubst ${vars_to_substitute} | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > ./docker/nginx.conf  &&
                 cat ./docker/templates/nginx-root.conf.template | envsubst ${vars_to_substitute} | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > ./docker/nginx-root.conf  &&
-                sudo docker run --network host --name wildcard-nginx -d -p 80:80 -p 443:443 -v `pwd`/docker/nginx-root.conf:/etc/nginx/nginx.conf -v `pwd`/docker/nginx.conf:/etc/nginx/conf.d/app.conf -v `pwd`/docker/_wildcard.appsmith.com.pem:/etc/certificate/dev.appsmith.com.pem -v `pwd`/docker/_wildcard.appsmith.com-key.pem:/etc/certificate/dev.appsmith.com-key.pem nginx:latest \
+                sudo docker run --network ${network_mode} --name wildcard-nginx -d -p 80:80 -p 443:443 -v `pwd`/docker/nginx-root.conf:/etc/nginx/nginx.conf -v `pwd`/docker/nginx.conf:/etc/nginx/conf.d/app.conf -v `pwd`/docker/_wildcard.appsmith.com.pem:/etc/certificate/dev.appsmith.com.pem -v `pwd`/docker/_wildcard.appsmith.com-key.pem:/etc/certificate/dev.appsmith.com-key.pem nginx:latest \
                 && echo "
     nginx is listening on port 443 and forwarding to port 3000
     visit https://dev.appsmith.com
@@ -62,7 +87,7 @@ case "${unameOut}" in
                 echo "
     Starting nginx for MacOS...
     "
-                cat ./docker/templates/nginx-mac.conf.template | envsubst ${vars_to_substitute} | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > ./docker/nginx.conf  &&
+                cat ./docker/templates/nginx-app.conf.template | sed -e "s|__APPSMITH_CLIENT_PROXY_PASS__|${client_proxy_pass}|g" | sed -e "s|__APPSMITH_SERVER_PROXY_PASS__|${server_proxy_pass}|g" | envsubst ${vars_to_substitute} | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > ./docker/nginx.conf  &&
                 cat ./docker/templates/nginx-root.conf.template | envsubst ${vars_to_substitute} | sed -e 's|\${\(APPSMITH_[A-Z0-9_]*\)}||g' > ./docker/nginx-root.conf  &&
                 docker run --name wildcard-nginx -d -p 80:80 -p 443:443 -v `pwd`/docker/nginx-root.conf:/etc/nginx/nginx.conf -v `pwd`/docker/nginx.conf:/etc/nginx/conf.d/app.conf -v `pwd`/docker/_wildcard.appsmith.com.pem:/etc/certificate/dev.appsmith.com.pem -v `pwd`/docker/_wildcard.appsmith.com-key.pem:/etc/certificate/dev.appsmith.com-key.pem nginx:latest \
                 && echo "