diff --git a/.travis.yml b/.travis.yml
index 7b87e251a2525..0365f5855e893 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -65,7 +65,7 @@ jobs:
         - ./bin/run-wp-unit-tests.sh
 
     - name: E2E tests (Admin with plugins) (1/2)
-      env: WP_VERSION=latest POPULAR_PLUGINS=true
+      env: WP_VERSION=latest SCRIPT_DEBUG=false POPULAR_PLUGINS=true
       install:
         - ./bin/setup-local-env.sh
       script:
@@ -74,7 +74,7 @@ jobs:
         - npm run test-e2e -- --ci --cacheDirectory="$HOME/.jest-cache" --runTestsByPath $( awk 'NR % 2 == 0' < ~/.jest-e2e-tests )
 
     - name: E2E tests (Admin with plugins) (2/2)
-      env: WP_VERSION=latest POPULAR_PLUGINS=true
+      env: WP_VERSION=latest SCRIPT_DEBUG=false POPULAR_PLUGINS=true
       install:
         - ./bin/setup-local-env.sh
       script:
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index da1c2c8e655dd..5cd10599b8087 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -79,10 +79,11 @@ Alternatively, you can use your own local WordPress environment and clone this r
 
 Next, open a terminal (or if on Windows, a command prompt) and navigate to the repository you cloned. Now type `npm install` to get the dependencies all set up. Then you can type `npm run dev` in your terminal or command prompt to keep the plugin building in the background as you work on it.
 
-WordPress comes with specific [debug systems](https://codex.wordpress.org/Debugging_in_WordPress) designed to simplify the process as well as standardize code across core, plugins and themes. It is possible to use environment variables (`WP_DEBUG`, `WP_DEBUG_DISPLAY` and `SCRIPT_DEBUG`) to update a site's configuration constants located in `wp-config.php` file. They can be updated at any time by running the following command:
+WordPress comes with specific [debug systems](https://codex.wordpress.org/Debugging_in_WordPress) designed to simplify the process as well as standardize code across core, plugins and themes. It is possible to use environment variables (`WP_DEBUG`, `WP_DEBUG_DISPLAY` and `SCRIPT_DEBUG`) to update a site's configuration constants located in `wp-config.php` file. Any of the flags can be disabled at any time by running the following command:
 ```
-SCRIPT_DEBUG=true WP_DEBUG=true WP_DEBUG_DISPLAY=true ./bin/setup-local-env.sh
+SCRIPT_DEBUG=false WP_DEBUG=false WP_DEBUG_DISPLAY=false ./bin/setup-local-env.sh
 ```
+By default, all 3 flags will be set to `true`.
 
 ### On A Remote Server
 
diff --git a/bin/bootstrap-env.sh b/bin/bootstrap-env.sh
index 6b3b1c9d29aee..733b78557fe0e 100755
--- a/bin/bootstrap-env.sh
+++ b/bin/bootstrap-env.sh
@@ -1,6 +1,9 @@
 #!/usr/bin/env bash
 
 WP_VERSION=${WP_VERSION-latest}
+WP_DEBUG=${WP_DEBUG-true}
+WP_DEBUG_DISPLAY=${WP_DEBUG_DISPLAY-true}
+SCRIPT_DEBUG=${SCRIPT_DEBUG-true}
 DOCKER=${DOCKER-false}
 DOCKER_ENV=${DOCKER_ENV-ci}
 DOCKER_COMPOSE_FILE_OPTIONS="-f docker-compose.yml"
diff --git a/bin/install-wordpress.sh b/bin/install-wordpress.sh
index 77c2591fdb433..eaaf60672f069 100755
--- a/bin/install-wordpress.sh
+++ b/bin/install-wordpress.sh
@@ -92,17 +92,20 @@ fi
 
 # Configure site constants.
 echo -e $(status_message "Configuring site constants...")
-if [ ! -z "$WP_DEBUG" ]; then
+WP_DEBUG_CURRENT=$(docker-compose $DOCKER_COMPOSE_FILE_OPTIONS run -T --rm -u 33 $CLI config get --type=constant --format=json WP_DEBUG)
+if [ $WP_DEBUG != $WP_DEBUG_CURRENT ]; then
 	docker-compose $DOCKER_COMPOSE_FILE_OPTIONS run --rm -u 33 $CLI config set WP_DEBUG $WP_DEBUG --raw --type=constant --quiet
 	WP_DEBUG_RESULT=$(docker-compose $DOCKER_COMPOSE_FILE_OPTIONS run -T --rm -u 33 $CLI config get --type=constant --format=json WP_DEBUG)
 	echo -e $(status_message "WP_DEBUG: $WP_DEBUG_RESULT...")
 fi
-if [ ! -z "$WP_DEBUG_DISPLAY" ]; then
+WP_DEBUG_DISPLAY_CURRENT=$(docker-compose $DOCKER_COMPOSE_FILE_OPTIONS run -T --rm -u 33 $CLI config get --type=constant --format=json WP_DEBUG_DISPLAY)
+if [ $WP_DEBUG_DISPLAY != $WP_DEBUG_DISPLAY_CURRENT ]; then
 	docker-compose $DOCKER_COMPOSE_FILE_OPTIONS run --rm -u 33 $CLI config set WP_DEBUG_DISPLAY $WP_DEBUG_DISPLAY --raw --type=constant --quiet
 	WP_DEBUG_DISPLAY_RESULT=$(docker-compose $DOCKER_COMPOSE_FILE_OPTIONS run -T --rm -u 33 $CLI config get --type=constant --format=json WP_DEBUG_DISPLAY)
 	echo -e $(status_message "WP_DEBUG_DISPLAY: $WP_DEBUG_DISPLAY_RESULT...")
 fi
-if [ ! -z "$SCRIPT_DEBUG" ]; then
+SCRIPT_DEBUG_CURRENT=$(docker-compose $DOCKER_COMPOSE_FILE_OPTIONS run -T --rm -u 33 $CLI config get --type=constant --format=json SCRIPT_DEBUG)
+if [ $SCRIPT_DEBUG != $SCRIPT_DEBUG_CURRENT ]; then
 	docker-compose $DOCKER_COMPOSE_FILE_OPTIONS run --rm -u 33 $CLI config set SCRIPT_DEBUG $SCRIPT_DEBUG --raw --type=constant --quiet
 	SCRIPT_DEBUG_RESULT=$(docker-compose $DOCKER_COMPOSE_FILE_OPTIONS run -T --rm -u 33 $CLI config get --type=constant --format=json SCRIPT_DEBUG)
 	echo -e $(status_message "SCRIPT_DEBUG: $SCRIPT_DEBUG_RESULT...")