diff --git a/justfile b/justfile
index 0056277..3f84982 100644
--- a/justfile
+++ b/justfile
@@ -1,5 +1,6 @@
 set positional-arguments
 set dotenv-load
+set export
 
 IMAGE := env_var_or_default("IMAGE", "debian-11")
 IMAGE_SRC := env_var_or_default("IMAGE_SRC", "debian-11")
diff --git a/nfpm.yaml b/nfpm.yaml
index e9a74fc..84bc679 100644
--- a/nfpm.yaml
+++ b/nfpm.yaml
@@ -23,6 +23,14 @@ contents:
       group: tedge
       owner: tedge
 
+  - src: ./src/tedge-monit-setup/env
+    dst: /etc/tedge-monit-setup/env
+    type: config|noreplace
+    file_info:
+      mode: 0644
+      group: root
+      owner: root
+
   - src: ./src/bin/monit-tedge-message
     dst: /usr/bin/
     file_info:
@@ -30,6 +38,13 @@ contents:
       group: root
       owner: root
 
+  - src: ./src/bin/monit-tedge-reconnect
+    dst: /usr/bin/
+    file_info:
+      mode: 0755
+      group: root
+      owner: root
+
 overrides:
   apk:
     depends:
diff --git a/src/bin/monit-tedge-reconnect b/src/bin/monit-tedge-reconnect
new file mode 100755
index 0000000..e18b4b1
--- /dev/null
+++ b/src/bin/monit-tedge-reconnect
@@ -0,0 +1,169 @@
+#!/bin/sh
+set -e
+
+help() {
+    cat << EOT
+Collect debug information and repair the given cloud connection
+
+$0 <c8y|aws|az>
+
+EXAMPLE
+
+    $0 c8y
+    # Repair the Cumulocity IoT cloud connection (and collect debug information)
+
+EOT
+}
+
+log() { echo "$@" >&2; }
+
+CLOUD=
+LOG_DIR=/var/log/tedge-monit-setup
+
+# Only read the file if it has the correct permissions, to prevent people from editing it
+# and side-loading functions
+SETTINGS_FILE=/etc/tedge-monit-setup/env
+FOUND_FILE=
+if [ -f "$SETTINGS_FILE" ]; then
+    FOUND_FILE=$(find "$SETTINGS_FILE" -perm 644 | head -n 1)
+fi
+
+if [ -n "$FOUND_FILE" ]; then
+    log "Loading setting file: $SETTINGS_FILE"
+    # shellcheck disable=SC1091,SC1090
+    . "$SETTINGS_FILE"
+fi
+
+#
+# Parse arguments
+#
+while [ $# -gt 0 ]; do
+    case "$1" in
+        -h|--help)
+            help
+            exit 0
+            ;;
+        --log-dir)
+            LOG_DIR="$2"
+            shift
+            ;;
+        --*|-*)
+            log "Unknown flag. $1"
+            help
+            exit 1
+            ;;
+        *)
+            if [ -z "$CLOUD" ]; then
+                CLOUD="$1"
+            fi
+            ;;
+    esac
+    shift
+done
+
+if [ -z "$CLOUD" ]; then
+    log "Cloud setting is empty"
+    help
+    exit 1
+fi
+
+remove_old_files() {
+    cd "$LOG_DIR"
+
+    MAX_FILES=${MAX_FILES:-10}
+    if [ "$MAX_FILES" -gt 0 ]; then
+    #     ls -t "$LOG_DIR"/*.tar.gz | tail +6 | xargs rm
+        find "$LOG_DIR" -name "tedge-debug-*.tar.gz" | tail +"$MAX_FILES" | xargs rm
+    fi
+
+    # Only keep files newer than x days (protect against an empty log dir)
+    MAX_DAYS="${MAX_DAYS:-30}"
+    if [ "$MAX_DAYS" -gt 0 ] && [ -n "$LOG_DIR" ]; then
+        find "$LOG_DIR" -name "tedge-debug-*.tar.gz" -mtime "$MAX_DAYS" -exec rm -f {} \; ||:
+    fi
+}
+
+pre_log_collection() {
+    #
+    # Collect logs before the corrective action has been executed
+    #
+    mkdir -p "$LOGD" ||:
+
+    journalctl -u "tedge-mapper-$CLOUD" -n 100 > "$LOGD/tedge-mapper-$CLOUD.log" ||:
+    journalctl -u tedge-agent -n 100 > "$LOGD/tedge-agent.log" ||:
+
+    tedge config list > "$LOGD/tedge-config-list.txt"
+
+    if [ -f /etc/tedge/.tedge-mapper-c8y/entity_store.jsonl ]; then
+        cp /etc/tedge/.tedge-mapper-c8y/entity_store.jsonl "$LOGD/" ||:
+    fi
+
+    if [ -f /var/log/mosquitto/mosquitto.log ]; then
+        tail -n 100 /var/log/mosquitto/mosquitto.log > "$LOGD/mosquitto.log" ||:
+    fi
+
+    monit summary > "$LOGD/monit.summary.txt" ||:
+    monit status > "$LOGD/monit.status.txt" ||:
+}
+
+post_log_collection() {
+    #
+    # Collect logs after the corrective action has been executed
+    #
+    mkdir -p "$LOGD" ||:
+
+    if command -V timeout >/dev/null 2>&1; then
+        timeout 5 tedge mqtt sub '#' > "$LOGD/mqtt.txt" ||:
+    fi
+}
+
+publish_event() {
+    attempt=0
+    code=1
+    while [ "$attempt" -lt 5 ]; do
+        if MONIT_EVENT="Reconnected to cloud ($CLOUD)" MONIT_DESCRIPTION="A monit rule was able to reconnect to the cloud. Check the $LOG_DIR directory for files" /usr/bin/monit-tedge-message event "${CLOUD}_reconnected"; then
+            code=0
+            break
+        fi
+        attempt=$((attempt + 1))
+        sleep 5
+    done
+    if [ "$code" != 0 ]; then
+        log "Warning: Could not publish reconnected event"
+    fi
+    return "$code"
+}
+
+LOGD="$LOG_DIR/tmp"
+log "Logging files to $LOGD"
+
+if ! remove_old_files; then
+    log "Unexpected error whilst cleaning up old log files"
+fi
+
+# Collect logs
+if ! pre_log_collection; then
+    log "Warning: Unkown error whilst collecting pre debug information"
+fi
+
+# Perform corrective action to try to reestablish the cloud connection
+tedge reconnect "$CLOUD"
+
+# send event so it is easier to query the cloud to find devices where a problem occurred
+publish_event ||:
+
+# Collect logs after the connection has hopefully been repaired
+if ! post_log_collection; then
+    log "Warning: Unknown error whilst collecting post debug information"
+fi
+
+# Compress archive
+LOG_NAME="$(date +"tedge-debug-${CLOUD}_%Y%m%d_%H%M")"
+cd "$LOGD" && tar czf "$LOG_DIR/${LOG_NAME}.tar.gz" .
+
+# Also create a concatenated log file so it can be retrieved via the log_upload operation
+if command -V zcat >/dev/null 2>&1; then
+    zcat "$LOG_DIR/${LOG_NAME}.tar.gz" > "$LOG_DIR/${LOG_NAME}.log"
+fi
+
+rm -rf "$LOGD"
diff --git a/src/conf.d/tedge-monitoring.conf b/src/conf.d/tedge-monitoring.conf
index 209e592..c536890 100644
--- a/src/conf.d/tedge-monitoring.conf
+++ b/src/conf.d/tedge-monitoring.conf
@@ -47,7 +47,7 @@ check program c8y-connectivity with path "/usr/bin/tedge connect c8y --test"
    with timeout 60 seconds
    every 120 cycles
    if status != 0 then alert
-   if status != 0 for 10 cycles then exec "/usr/bin/tedge reconnect c8y"
+   if status != 0 for 10 cycles then exec "/usr/bin/monit-tedge-reconnect c8y"
    depends on c8y-enabled
    group c8y
 
@@ -64,7 +64,7 @@ check program az-connectivity with path "/usr/bin/tedge connect az --test"
    with timeout 60 seconds
    every 120 cycles
    if status != 0 then alert
-   if status != 0 for 10 cycles then exec "/usr/bin/tedge reconnect az"
+   if status != 0 for 10 cycles then exec "/usr/bin/monit-tedge-reconnect az"
    depends on az-enabled
    group az
 
@@ -81,6 +81,6 @@ check program aws-connectivity with path "/usr/bin/tedge connect aws --test"
    with timeout 60 seconds
    every 120 cycles
    if status != 0 then alert
-   if status != 0 for 10 cycles then exec "/usr/bin/tedge reconnect aws"
+   if status != 0 for 10 cycles then exec "/usr/bin/monit-tedge-reconnect aws"
    depends on aws-enabled
    group aws
diff --git a/src/tedge-monit-setup/env b/src/tedge-monit-setup/env
new file mode 100644
index 0000000..7de999e
--- /dev/null
+++ b/src/tedge-monit-setup/env
@@ -0,0 +1,8 @@
+# Where to write the log files to
+#LOG_DIR=/var/log/tedge-monit-setup
+
+# Maximum number of days to keep log (tar.gz) files
+#MAX_DAYS=30
+
+# Maximum number of log (tar.gz) files to keep
+#MAX_FILES=10
diff --git a/tests/monit.robot b/tests/monit.robot
index bcf9087..e2b56b9 100644
--- a/tests/monit.robot
+++ b/tests/monit.robot
@@ -20,6 +20,10 @@ Reconnect on cloud connection loss (by stopping mosquitto)
     Execute Command    tedge connect c8y --test    timeout=120
     Execute Command    systemctl is-active mosquitto
     Execute Command    systemctl is-active tedge-mapper-c8y
+    Cumulocity.Device Should Exist    ${DEVICE_SN}
+    Cumulocity.Device Should Have Event/s    expected_text=.*Reconnected to cloud .*c8y.*    type=c8y_reconnected
+    Assert File Count    /var/log/tedge-monit-setup/*.tar.gz    1
+    Assert File Count    /var/log/tedge-monit-setup/*.log    1
 
 
 *** Keywords ***
@@ -35,3 +39,7 @@ Decrease monit intervals
     Execute Command    cmd=sed -i 's/every 120 cycles/every 5 cycles/g' /etc/monit/conf.d/tedge-monitoring.conf
     Execute Command    cmd=sed -i 's/if status != 0 for 10 cycles/if status != 0 for 2 cycles/g' /etc/monit/conf.d/tedge-monitoring.conf
     Execute Command    systemctl restart monit
+
+Assert File Count
+    [Arguments]    ${path}    ${count}
+    DeviceLibrary.Execute Command    cmd=[ $(ls -l ${path} | wc -l | xargs) = ${count} ]