diff --git a/scripts/.gitignore b/scripts/.gitignore
new file mode 100644
index 00000000..79cef29c
--- /dev/null
+++ b/scripts/.gitignore
@@ -0,0 +1 @@
+wait4x
diff --git a/scripts/common.Makefile b/scripts/common.Makefile
index 86d008b8..5f3f4517 100644
--- a/scripts/common.Makefile
+++ b/scripts/common.Makefile
@@ -342,8 +342,13 @@ show-venv: venv  ## show venv info
 	@echo venv: $(VENV_DIR)
 
 .PHONY: install
-install: requirements.txt venv ## install dependencies from ./requirements.txt
-	@VIRTUAL_ENV=$(VENV_DIR) $(UV) pip install --requirement $<
+install: guard-optional-REQUIREMENTS_FILE venv ## install requirements.txt dependencies
+	@if [ -z "$(REQUIREMENTS_FILE)" ]; then \
+		REQUIREMENTS_FILE=./requirements.txt; \
+	else \
+		REQUIREMENTS_FILE=$(REQUIREMENTS_FILE); \
+	fi; \
+	VIRTUAL_ENV=$(VENV_DIR) $(UV) pip install --requirement $$REQUIREMENTS_FILE
 
 # https://github.com/kolypto/j2cli?tab=readme-ov-file#customization
 ifeq ($(shell test -f j2cli_customization.py && echo -n yes),yes)
@@ -362,3 +367,21 @@ define jinja
 endef
 
 endif
+
+#
+# wait-fot-it functionality
+#
+
+WAIT_FOR_IT := $(REPO_BASE_DIR)/scripts/wait4x
+
+alias: $(WAIT_FOR_IT)
+
+# https://github.com/wait4x/wait4x
+$(WAIT_FOR_IT):  ## installs wait4x utility for WAIT_FOR_IT functionality
+	# installing wait4x
+	@mkdir --parents /tmp/wait4x
+	@cd /tmp/wait4x && curl --silent --location --remote-name https://github.com/wait4x/wait4x/releases/download/v3.5.0/wait4x-linux-amd64.tar.gz
+	@tar -xf /tmp/wait4x/wait4x-linux-amd64.tar.gz -C /tmp/wait4x
+	@mv /tmp/wait4x/wait4x $@
+	@rm -rf /tmp/wait4x
+	@$@ version
diff --git a/services/monitoring/grafana/Makefile b/services/monitoring/grafana/Makefile
index 0c088ed1..d6db6db3 100644
--- a/services/monitoring/grafana/Makefile
+++ b/services/monitoring/grafana/Makefile
@@ -39,29 +39,11 @@ terraform-apply: $(REPO_CONFIG_LOCATION) terraform/plan.cache $(TF_STATE_FILE) e
 	terraform -chdir=./terraform apply plan.cache
 
 .PHONY: ensure-grafana-online
-ensure-grafana-online:
+ensure-grafana-online: $(WAIT_FOR_IT)
 	@set -o allexport; \
 	source $(REPO_CONFIG_LOCATION); \
 	set +o allexport; \
-	url=$${TF_VAR_GRAFANA_URL}; \
-	echo "Waiting for grafana at $$url to become reachable..."; \
-	attempts=0; \
-	max_attempts=10; \
-	while [ $$attempts -lt $$max_attempts ]; do \
-		status_code=$$(curl -k -o /dev/null -s -w "%{http_code}" --max-time 10 $$url); \
-		if [ "$$status_code" -ge 200 ] && [ "$$status_code" -lt 400 ]; then \
-			echo "Grafana is online"; \
-			break; \
-		else \
-			echo "Grafana still unreachable, waiting 5s for grafana to become reachable... (Attempt $$((attempts+1)))"; \
-			sleep 5; \
-			attempts=$$((attempts + 1)); \
-		fi; \
-	done; \
-	if [ $$attempts -eq $$max_attempts ]; then \
-		echo "Max attempts reached, Grafana is still unreachable."; \
-		exit 1; \
-	fi;
+	$(WAIT_FOR_IT) http $$TF_VAR_GRAFANA_URL --timeout=120s --interval=5s --expect-status-code 200
 
 .PHONY: assets
 assets: ${REPO_CONFIG_LOCATION}
diff --git a/services/portainer/Makefile b/services/portainer/Makefile
index 9337e5d3..33520b87 100644
--- a/services/portainer/Makefile
+++ b/services/portainer/Makefile
@@ -15,26 +15,22 @@ include ${REPO_BASE_DIR}/scripts/common.Makefile
 .PHONY: up ## Deploys portainer stack
 up: .init .env secrets ${TEMP_COMPOSE}
 	@docker stack deploy --with-registry-auth --prune --compose-file ${TEMP_COMPOSE} ${STACK_NAME}
+	@$(MAKE) --noprint configure-portainer-registry
 
 .PHONY: up-local ## Deploys portainer stack for local deployment
 up-local: .init .env secrets ${TEMP_COMPOSE} ${TEMP_COMPOSE}-local
 	@docker stack deploy --with-registry-auth --prune --compose-file ${TEMP_COMPOSE}-local ${STACK_NAME}
-
-.PHONY: up-letsencrypt-http ## Deploys portainer stack using let's encrypt http challenge
-up-letsencrypt-http: .init .env secrets ${TEMP_COMPOSE}-letsencrypt-http
-	@docker stack deploy --with-registry-auth --prune --compose-file ${TEMP_COMPOSE}-letsencrypt-http ${STACK_NAME}
-
-.PHONY: up-letsencrypt-dns ## Deploys portainer stack using let's encrypt dns challenge
-up-letsencrypt-dns: .init .env secrets ${TEMP_COMPOSE}-letsencrypt-dns
-	@docker stack deploy --with-registry-auth --prune --compose-file ${TEMP_COMPOSE}-letsencrypt-dns ${STACK_NAME}
+	@$(MAKE) --noprint configure-portainer-registry
 
 .PHONY: up-dalco ## Deploys portainer stack for Dalco Cluster
 up-dalco: .init .env secrets ${TEMP_COMPOSE}-dalco
 	@docker stack deploy --with-registry-auth --prune --compose-file ${TEMP_COMPOSE}-dalco ${STACK_NAME}
+	@$(MAKE) --noprint configure-portainer-registry
 
 .PHONY: up-aws ## Deploys portainer stack for AWS
 up-aws: .init .env secrets ${TEMP_COMPOSE}-aws
 	@docker stack deploy --with-registry-auth --prune --compose-file ${TEMP_COMPOSE}-aws ${STACK_NAME}
+	@$(MAKE) --noprint configure-portainer-registry
 
 .PHONY: up-public ## Deploys portainer stack for public access Cluster
 up-public: up-dalco
@@ -42,23 +38,15 @@ up-public: up-dalco
 .PHONY: up-master ## Deploys portainer stack for master Cluster
 up-master: .init .env secrets ${TEMP_COMPOSE}-master
 	@docker stack deploy --with-registry-auth --prune --compose-file ${TEMP_COMPOSE}-master ${STACK_NAME}
+	@$(MAKE) --noprint configure-portainer-registry
 
 
-.PHONY: configure-registry
-configure-registry:  ## Add if necessary dockerhub registry configuration to portainer.
-	@set -o allexport; \
-	source $(REPO_CONFIG_LOCATION); \
-	set +o allexport; \
-	while [ "$$(curl -s -o /dev/null -I -w "%{http_code}" --max-time 10  -H "Accept: application/json" -H "Content-Type: application/json" -X GET https://"$$MONITORING_DOMAIN"/portainer/#/auth)" != 200 ]; do\
-		echo "waiting for portainer to run...";\
-		sleep 5s;\
-	done;\
-	echo "Updating docker-hub config";\
-	authentificationToken=$$(curl -o /dev/null -X POST "https://"$$MONITORING_DOMAIN"/portainer/api/auth" -H  "Content-Type: application/json" -d "{  \"Username\": \"$${PORTAINER_ADMIN_LOGIN}\",  \"Password\": \"$${PORTAINER_ADMIN_PWD}\"}"); \
-	authentificationToken=$$(echo "$$authentificationToken" | jq --raw-output '.jwt'); \
-	update_hub=$$(curl -o /dev/null -X PUT "https://"$$MONITORING_DOMAIN"/portainer/api/dockerhub" -H  "accept: application/json" -H \
-	"Authorization: Bearer $${authentificationToken}" -H  "Content-Type: application/json" \
-	-d "{  \"Authentication\": true,  \"Username\": \"$$DOCKER_HUB_LOGIN\",  \"Password\": \"$$DOCKER_HUB_PASSWORD\"}"); \
+.PHONY: configure-portainer-registry
+configure-portainer-registry: venv $(VENV_BIN)/python $(WAIT_FOR_IT) ## Add registry to Portainer
+	@$(MAKE) --no-print install REQUIREMENTS_FILE=./scripts/requirements.txt
+	@set -o allexport; source $(REPO_CONFIG_LOCATION); set +o allexport; \
+	$(WAIT_FOR_IT) http $$PORTAINER_URL --timeout=120s --interval=5s --expect-status-code 200 && \
+	$(VENV_BIN)/python ./scripts/configure_portainer_registry.py
 
 
 # Helpers -------------------------------------------------
@@ -67,14 +55,6 @@ configure-registry:  ## Add if necessary dockerhub registry configuration to por
 ${TEMP_COMPOSE}: docker-compose.yml .env
 	@${REPO_BASE_DIR}/scripts/docker-stack-config.bash -e .env $< > $@
 
-.PHONY: ${TEMP_COMPOSE}-letsencrypt-http
-${TEMP_COMPOSE}-letsencrypt-http: docker-compose.yml docker-compose.letsencrypt.http.yml .env
-	@${REPO_BASE_DIR}/scripts/docker-stack-config.bash -e .env $< docker-compose.letsencrypt.http.yml > $@
-
-.PHONY: ${TEMP_COMPOSE}-letsencrypt-dns
-${TEMP_COMPOSE}-letsencrypt-dns: docker-compose.yml docker-compose.letsencrypt.dns.yml .env
-	@${REPO_BASE_DIR}/scripts/docker-stack-config.bash -e .env $< docker-compose.letsencrypt.dns.yml > $@
-
 .PHONY: ${TEMP_COMPOSE}-dalco
 ${TEMP_COMPOSE}-dalco: docker-compose.yml docker-compose.dalco.yml .env
 	@${REPO_BASE_DIR}/scripts/docker-stack-config.bash -e .env $< docker-compose.dalco.yml  > $@
diff --git a/services/portainer/docker-compose.letsencrypt.dns.yml b/services/portainer/docker-compose.letsencrypt.dns.yml
deleted file mode 100644
index 88fbcdb6..00000000
--- a/services/portainer/docker-compose.letsencrypt.dns.yml
+++ /dev/null
@@ -1,6 +0,0 @@
-version: "3.7"
-services:
-  portainer:
-    deploy:
-      labels:
-        - traefik.http.routers.portainer.tls.certresolver=myresolver
diff --git a/services/portainer/docker-compose.letsencrypt.http.yml b/services/portainer/docker-compose.letsencrypt.http.yml
deleted file mode 100644
index 74cf115f..00000000
--- a/services/portainer/docker-compose.letsencrypt.http.yml
+++ /dev/null
@@ -1,6 +0,0 @@
-version: "3.7"
-services:
-  portainer:
-    deploy:
-      labels:
-        - traefik.http.routers.portainer.tls.certresolver=lehttpchallenge
diff --git a/services/portainer/scripts/configure_portainer_registry.py b/services/portainer/scripts/configure_portainer_registry.py
new file mode 100644
index 00000000..017076e8
--- /dev/null
+++ b/services/portainer/scripts/configure_portainer_registry.py
@@ -0,0 +1,138 @@
+import logging
+import os
+from enum import Enum
+from typing import TypedDict
+
+import requests
+from tenacity import retry
+
+logger = logging.getLogger(__name__)
+
+
+# https://app.swaggerhub.com/apis/portainer/portainer-ce/2.27.6#/portainer.Registry
+class RegistryType(Enum):
+    DOCKER_HUB = 6
+
+
+class Registry(TypedDict):
+    Id: int
+    Name: str
+    URL: str
+    Authentication: bool
+    Username: str
+    Type: RegistryType
+
+
+@retry
+def get_portainer_api_auth_token(
+    portainer_api_url: str, portainer_username: str, portainer_password: str
+) -> str:
+    # https://app.swaggerhub.com/apis/portainer/portainer-ce/2.27.6#/auth/AuthenticateUser
+    response = requests.post(
+        f"{portainer_api_url}/auth",
+        # https://app.swaggerhub.com/apis/portainer/portainer-ce/2.27.6#/auth.authenticatePayload
+        json={"Username": portainer_username, "Password": portainer_password},
+    )
+
+    try:
+        response.raise_for_status()
+    except requests.HTTPError as e:
+        logger.error("Failed to authenticate with Portainer API: %s", e.response.text)
+        raise
+
+    return response.json()["jwt"]
+
+
+@retry
+def get_registries(portainer_api_url: str, auth_token: str) -> list[Registry]:
+    # https://app.swaggerhub.com/apis/portainer/portainer-ce/2.27.6#/registries/RegistryList
+    response = requests.get(
+        f"{portainer_api_url}/registries",
+        headers={"Authorization": f"Bearer {auth_token}"},
+    )
+
+    try:
+        response.raise_for_status()
+    except requests.HTTPError as e:
+        logger.error("Failed to fetch registries: %s", e.response.text)
+        raise
+
+    return response.json()
+
+
+@retry
+def create_authenticated_dockerhub_registry(
+    portainer_api_url: str,
+    auth_token: str,
+    dockerhub_username: str,
+    dockerhub_password: str,
+    registry_name: str = "IT'IS Foundation",
+) -> None:
+    # https://app.swaggerhub.com/apis/portainer/portainer-ce/2.27.6#/registries/RegistryCreate
+    response = requests.post(
+        f"{portainer_api_url}/registries",
+        headers={"Authorization": f"Bearer {auth_token}"},
+        # https://app.swaggerhub.com/apis/portainer/portainer-ce/2.27.6#/registries.registryCreatePayload
+        json={
+            "name": registry_name,
+            "url": "docker.io",
+            "authentication": True,
+            "username": dockerhub_username,
+            "password": dockerhub_password,
+            "type": RegistryType.DOCKER_HUB.value,
+        },
+    )
+
+    try:
+        response.raise_for_status()
+    except requests.HTTPError as e:
+        logger.error(
+            "Failed to create authenticated Docker Hub registry: %s", e.response.text
+        )
+        raise
+
+    return response.json()
+
+
+def main():
+    logger.info("Configuring Portainer registries...")
+
+    portainer_username = os.environ["SERVICES_USER"]
+    portainer_password = os.environ["SERVICES_PASSWORD"]
+    portainer_api_url = os.environ["PORTAINER_URL"] + "/api"
+
+    dockerhub_username = os.environ["DOCKER_HUB_LOGIN"]
+    dockerhub_password = os.environ["DOCKER_HUB_PASSWORD"]
+
+    portainer_jwt_token = get_portainer_api_auth_token(
+        portainer_api_url, portainer_username, portainer_password
+    )
+
+    registries = get_registries(portainer_api_url, portainer_jwt_token)
+
+    if not any(
+        r["Type"] == RegistryType.DOCKER_HUB.value and r["Authentication"] is True
+        for r in registries
+    ):
+        logging.info("Creating authenticated Docker Hub registry in Portainer...")
+        create_authenticated_dockerhub_registry(
+            portainer_api_url,
+            portainer_jwt_token,
+            dockerhub_username,
+            dockerhub_password,
+        )
+    else:
+        logging.info("Portainer already has an authenticated Docker Hub registry.")
+
+    logging.info("Portainer registries configuration completed.")
+
+
+def configure_logging():
+    logging.basicConfig(
+        level=logging.INFO,
+    )
+
+
+if __name__ == "__main__":
+    configure_logging()
+    main()
diff --git a/services/portainer/scripts/requirements.txt b/services/portainer/scripts/requirements.txt
new file mode 100644
index 00000000..e58f026e
--- /dev/null
+++ b/services/portainer/scripts/requirements.txt
@@ -0,0 +1,2 @@
+tenacity==9.1.2
+requests==2.32.4