diff --git a/server/Dockerfile b/server/Dockerfile
index 2855cc0..7859eb4 100644
--- a/server/Dockerfile
+++ b/server/Dockerfile
@@ -1,7 +1,7 @@
 # ------------------------------------------------------------------------------
 # Build go-flare
 # ------------------------------------------------------------------------------
-FROM golang:1.18.5 AS flare
+FROM golang:1.21 AS flare
 
 WORKDIR /app
 
@@ -18,7 +18,7 @@ RUN cd avalanchego && \
 # ------------------------------------------------------------------------------
 # Build flare-rosetta
 # ------------------------------------------------------------------------------
-FROM golang:1.18.5 AS rosetta
+FROM golang:1.21 AS rosetta
 
 ARG ROSETTA_SRC=https://github.com/flare-foundation/flare-rosetta/archive/refs/heads/main.zip
 ARG ROSETTA_SRC_ZIP_SUBFOLDER=flare-rosetta-main
@@ -50,7 +50,7 @@ RUN \
 # ------------------------------------------------------------------------------
 # Target container for running the rosetta server
 # ------------------------------------------------------------------------------
-FROM ubuntu:20.04
+FROM ubuntu@sha256:340d9b015b194dc6e2a13938944e0d016e57b9679963fdeb9ce021daac430221
 
 ENV DEBIAN_FRONTEND=noninteractive
 
diff --git a/server/docker/entrypoint_main.sh b/server/docker/entrypoint_main.sh
index 9ff2689..55a8c96 100644
--- a/server/docker/entrypoint_main.sh
+++ b/server/docker/entrypoint_main.sh
@@ -8,13 +8,20 @@ PID_ENTRYPOINT_FLARE=""
 
 function cleanup ()
 {
+    if kill -0 "$PID_ENTRYPOINT_FLARE"; then
+        echo "Flare process detected as exited"
+    fi
+
+    if kill -0 "$PID_ENTRYPOINT_ROSETTA"; then
+        echo "Rosetta process detected as exited"
+    fi
+
     if [ ! -z "${PID_ENTRYPOINT_ROSETTA}" ]; then echo "Sending KILL to ROSETTA entrypoint (pid:${PID_ENTRYPOINT_ROSETTA})..."; kill -SIGINT ${PID_ENTRYPOINT_ROSETTA}; fi
     if [ ! -z "${PID_ENTRYPOINT_FLARE}" ]; then echo "Sending KILL to FLARE entrypoint (pid:${PID_ENTRYPOINT_FLARE})..."; kill -SIGINT ${PID_ENTRYPOINT_FLARE}; fi
 }
 
 trap cleanup SIGINT
 
-
 if [ "$MODE" != "online" ] && [ "$MODE" != "offline" ]; then
     echo "An invalid value ('${MODE}') was provided for MODE env variable! Exiting..."
     exit 1
@@ -22,17 +29,22 @@ fi
 
 
 if [ "$MODE" = "online" ]; then
+    echo "Starting flare node in ONLINE mode"
     ./entrypoint_flare.sh | sed -e 's/^/[go-flare]: /;' &
     PID_ENTRYPOINT_FLARE=$!
 fi
 
+echo "Starting rosetta server"
 ./entrypoint_rosetta.sh | sed -e 's/^/[rosetta]: /;' &
 PID_ENTRYPOINT_ROSETTA=$!
 
 # Wait for any process to exit
+echo "Waiting for either process to exit"
 wait -n
 EXIT_CODE=$?
 
+echo "Cleaning up and terminating processes due to exit code $EXIT_CODE"
+
 # Attempt to gracefully stop the other process
 cleanup
 
diff --git a/server/docker/entrypoint_rosetta.sh b/server/docker/entrypoint_rosetta.sh
index 492724b..53981be 100644
--- a/server/docker/entrypoint_rosetta.sh
+++ b/server/docker/entrypoint_rosetta.sh
@@ -17,7 +17,8 @@ fi
 if [ "$MODE" = "online" ]; then
 
     # Wait for go-flare port to bind
-    curl ${ROSETTA_FLARE_ENDPOINT} --retry 6 --retry-connrefused --connect-timeout 5 --retry-delay 10 --silent --output /dev/null
+    sleep 30
+    curl ${ROSETTA_FLARE_ENDPOINT} --retry 6 --retry-connrefused --retry-all-errors --connect-timeout 5 --retry-delay 10 --silent --output /dev/null
 
     if [ "$START_ROSETTA_SERVER_AFTER_BOOTSTRAP" == "true" ]; then
         while true; do