diff --git a/advanced/Scripts/piholeDebug.sh b/advanced/Scripts/piholeDebug.sh
index fae7c0b9..70d73379 100755
--- a/advanced/Scripts/piholeDebug.sh
+++ b/advanced/Scripts/piholeDebug.sh
@@ -332,11 +332,17 @@ debugLighttpd() {
 }
 
 countdown() {
+  local tuvix
   tuvix=${TIMEOUT}
-  printf "::: Logging will automatically teminate in ${TIMEOUT} seconds\n"
+  printf "::: Logging will automatically teminate in %s seconds\n" "${TIMEOUT}"
   while [ $tuvix -ge 1 ]
   do
-    printf ":::\t${tuvix} seconds left. \r"
+    printf ":::\t%s seconds left. " "${tuvix}"
+    if [[ -z "${WEBCALL}" ]]; then
+      printf "\r"
+    else
+      printf "\n"
+    fi
     sleep 5
     tuvix=$(( tuvix - 5 ))
   done
@@ -407,20 +413,24 @@ finalWork() {
   local tricorder
 	echo "::: Finshed debugging!"
 	echo "::: The debug log can be uploaded to tricorder.pi-hole.net for sharing with developers only."
-	read -r -p "::: Would you like to upload the log? [y/N] " response
-	case ${response} in
-		[yY][eE][sS]|[yY])
-			tricorder=$(cat /var/log/pihole_debug.log | nc tricorder.pi-hole.net 9999)
-			;;
-		*)
-			echo "::: Log will NOT be uploaded to tricorder."
-			;;
-	esac
-
+	if [[ "${AUTOMATED}" ]]; then
+	  echo "::: Debug script running in automated mode, uploading log to tricorder..."
+	  tricorder=$(cat /var/log/pihole_debug.log | nc tricorder.pi-hole.net 9999)
+	else
+	  read -r -p "::: Would you like to upload the log? [y/N] " response
+	  case ${response} in
+		  [yY][eE][sS]|[yY])
+			  tricorder=$(cat /var/log/pihole_debug.log | nc tricorder.pi-hole.net 9999)
+			  ;;
+		  *)
+			  echo "::: Log will NOT be uploaded to tricorder."
+			  ;;
+	  esac
+  fi
 	# Check if tricorder.pi-hole.net is reachable and provide token.
 	if [ -n "${tricorder}" ]; then
-		echo "::: Your debug token is : ${tricorder}"
-		echo "::: Please contact the Pi-hole team with your token for assistance."
+		echo "::: ---=== Your debug token is : ${tricorder} Please make a note of it. ===---"
+		echo "::: Contact the Pi-hole team with your token for assistance."
 		echo "::: Thank you."
 	else
 		echo "::: There was an error uploading your debug log."
diff --git a/pihole b/pihole
index b79ab2b7..41946f35 100755
--- a/pihole
+++ b/pihole
@@ -45,7 +45,19 @@ wildcardFunc() {
 }
 
 debugFunc() {
-  "${PI_HOLE_SCRIPT_DIR}"/piholeDebug.sh
+  local automated
+  local web
+
+  # Pull off the `debug` leaving passed call augmentation flags in $1
+  shift
+  if [[ "$@" == *"-a"* ]]; then
+    automated="true"
+  fi
+  if [[ "$@" == *"-w"* ]]; then
+    web="true"
+  fi
+
+  AUTOMATED=${automated:-} WEBCALL=${web:-} "${PI_HOLE_SCRIPT_DIR}"/piholeDebug.sh
   exit 0
 }
 
@@ -278,6 +290,8 @@ helpFunc() {
 :::  -b, blacklist            Blacklist domain(s) (exact match)
 :::  -wild, wildcard          Blacklist whole domain(s) (wildcard)
 :::  -d, debug                Start a debugging session
+:::                             Automated debugging can be enabled with `-a`.
+:::                             'pihole -d -a'
 :::  -f, flush                Flush the 'pihole.log' file
 :::  -t, tail                 Output the last lines of the 'pihole.log' file. Lines are appended as the file grows
 :::  -up, updatePihole        Update Pi-hole components
@@ -287,15 +301,15 @@ helpFunc() {
 :::  -h, help                 Show this help dialog
 :::  -v, version              Show installed versions of Pi-Hole and Web-Admin
 :::  -q, query                Query the adlists for a specific domain
-:::                           Use 'pihole -q domain -exact' if you want to see exact matches only
+:::                             'pihole -q domain -exact' shows exact matches only
 :::  -l, logging              Enable or Disable logging (pass 'on' or 'off')
 :::  -a, admin                Admin webpage options
 :::  uninstall                Uninstall Pi-Hole from your system :(!
 :::  status                   Is Pi-Hole Enabled or Disabled
 :::  enable                   Enable Pi-Hole DNS Blocking
 :::  disable                  Disable Pi-Hole DNS Blocking
-:::                           Blocking can also be disabled only temporarily, e.g.,
-:::                           'pihole disable 5m' - will disable blocking for 5 minutes
+:::                             Blocking can also be disabled only temporarily, e.g.,
+:::                             'pihole disable 5m' - will disable blocking for 5 minutes
 :::  restartdns               Restart dnsmasq
 EOM
   exit 0
@@ -310,7 +324,7 @@ case "${1}" in
   "-w" | "whitelist"            ) whitelistFunc "$@";;
   "-b" | "blacklist"            ) blacklistFunc "$@";;
   "-wild" | "wildcard"          ) wildcardFunc "$@";;
-  "-d" | "debug"                ) debugFunc;;
+  "-d" | "debug"                ) debugFunc "$@";;
   "-f" | "flush"                ) flushFunc;;
   "-up" | "updatePihole"        ) updatePiholeFunc;;
   "-r"  | "reconfigure"         ) reconfigurePiholeFunc;;