diff --git a/.gitignore b/.gitignore
index 9e67b269c21d..1d41f4e216f6 100644
--- a/.gitignore
+++ b/.gitignore
@@ -69,3 +69,5 @@ dump.rdb
 ui-debug.log
 firebase-debug.log
 debug.log
+# development logs and status entries
+.dev
diff --git a/Makefile b/Makefile
index 547e00952127..90488f30793e 100644
--- a/Makefile
+++ b/Makefile
@@ -46,15 +46,14 @@ run-devserver: ## Runs the dev-server
 	docker compose stop angular-build
 	docker compose up dev-server -d --no-deps
 	$(MAKE) update.requirements
-	$(MAKE) run-offline
+	$(MAKE) start-devserver
 
 run-offline: ## Runs the dev-server in offline mode
+	## Users can pass this check by simply running `make start-devserver`
+	$(MAKE) check.dev-container-healthy
 	$(MAKE) start-devserver
-	@echo 'Please visit http://localhost:8181 to access the development server.'
-	@echo 'Check dev-server logs using "make logs.dev-server"'
-	@echo 'Stop the development server using "make stop"'
 
-start-devserver: ## Starts the development server for the tests
+start-devserver: ## Starts the development server
 	docker compose up dev-server -d
 	@printf 'Please wait while the development server starts...\n\n'
 	@while [[ $$(curl -s -o /tmp/status_code.txt -w '%{http_code}' http://localhost:8181) != "200" ]] || [[ $$(curl -s -o /tmp/status_code.txt -w '%{http_code}' http://localhost:8181/community-library) != "200" ]]; do \
@@ -65,7 +64,9 @@ start-devserver: ## Starts the development server for the tests
 		sleep 1; \
 	done
 	@printf '\n\n'
-	@echo 'Development server started at port 8181.'
+	@echo 'Please visit http://localhost:8181 to access the development server.'
+	@echo 'Check dev-server logs using "make logs.dev-server"'
+	@echo 'Stop the development server using "make stop"'
 
 init: build run-devserver ## Initializes the build and runs dev-server.
 
@@ -95,6 +96,20 @@ update.package: ## Installs the npm requirements for the project
 	@echo 'yarn-path "../oppia_tools/yarn-1.22.15/bin/yarn"' > .yarnrc
 	@echo 'cache-folder "../yarn_cache"' >> .yarnrc
 
+check.dev-container-healthy:
+	@run_devserver_prompt="Please, run \`make run-devserver\` (requires internet) once before running \`make run-offline\`"; \
+	if [ -f ".dev/containers-health.json" ]; then \
+		if jq -e ".devserver != true" ".dev/containers-health.json" > /dev/null; then \
+			echo "Container is unhealthy"; \
+			echo $$run_devserver_prompt; \
+			exit 1; \
+		fi \
+	else \
+		echo "Can't check container health!"; \
+		echo $$run_devserver_prompt; \
+		exit 1; \
+	fi
+
 logs.%: ## Shows the logs of the given docker service. Example: make logs.datastore
 	docker compose logs -f $*
 
diff --git a/docker-compose.yml b/docker-compose.yml
index f2797b0868f2..74bf312cfb53 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -74,7 +74,7 @@ services:
       - firebase
       - redis
     healthcheck:
-      test: curl -f http://localhost:8181/ || exit 1
+      test: ["CMD", "bash", "docker/dev-server.healthcheck.sh"]
       timeout: 10s
       interval: 30s
       retries: 5
diff --git a/docker/Dockerfile.backend b/docker/Dockerfile.backend
index 19d0cc598df1..39483cb8ac09 100644
--- a/docker/Dockerfile.backend
+++ b/docker/Dockerfile.backend
@@ -14,7 +14,8 @@ RUN apt-get update -y && apt-get upgrade -y \
     python2 \
     python3-matplotlib \
     unzip \
-    wget
+    wget \
+    jq
 RUN curl -sL https://deb.nodesource.com/setup_16.x | bash -
 RUN apt-get install -y nodejs
 
diff --git a/docker/dev-server.healthcheck.sh b/docker/dev-server.healthcheck.sh
new file mode 100644
index 000000000000..8adc9391dfb5
--- /dev/null
+++ b/docker/dev-server.healthcheck.sh
@@ -0,0 +1,50 @@
+#!/bin/bash
+# Copyright 2023 The Oppia Authors. All Rights Reserved.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS-IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+FILE=".dev/containers-health.json"
+
+# Create parent directories if needed
+DIR=$(dirname "$FILE")
+if [ ! -d "$DIR" ]; then
+  mkdir -p "$DIR"
+fi
+
+# Check and create file
+echo '{ "devserver": false }' > "$FILE"
+
+# Check if devserver health is stored and reset it to false
+key_to_check="devserver"
+if jq -e "has(\"$key_to_check\")" "$FILE" > /dev/null; then
+    jq '.["devserver"] = false' "$FILE" > /tmp/status.json && mv /tmp/status.json "$FILE"
+else
+    jq '. + { "devserver": false }' "$FILE" > /tmp/status.json && mv /tmp/status.json "$FILE"
+fi
+
+# Check container health
+curl -f http://localhost:8181/
+STATUS=$?
+
+if [ $STATUS -eq 0 ]; then
+  # Healthy 
+  jq '.["devserver"] = true' "$FILE" > /tmp/status.json && mv /tmp/status.json "$FILE"
+  
+  exit 0
+
+else
+  # Unhealthy
+  jq '.["devserver"] = false' "$FILE" > /tmp/status.json && mv /tmp/status.json "$FILE"
+
+  exit 1 
+fi