diff --git a/CHANGELOG.txt b/CHANGELOG.txt
index 6b6e367802..379a8570b4 100644
--- a/CHANGELOG.txt
+++ b/CHANGELOG.txt
@@ -21,6 +21,7 @@ Changes / Improvements / Optimisations:
 - DietPi-Software | Tor/WiFi Hotspot: Resolved an issue where WiFi Hotspot fails to start when Tor Hotspot is installed. Many thanks to @schnuckz for reporting this issue: https://github.com/MichaIng/DietPi/issues/2673#issuecomment-482605700
 
 Bug Fixes:
+- System | Debian has vastly reduced support for Jessie systems from their official APT repository. The limited possible list entries are applied during DietPi-Update. Many thanks to @BerndKohl for reporting this issue: https://github.com/MichaIng/DietPi/issues/2665
 - DietPi-Set_swapfile | Resolved an issue where on first boot (and when calling the script manually) the swapfile creation is attempted on target file systems that do not support it (BTRFS). Many thanks to @mzramna for reporting this issue: https://github.com/MichaIng/DietPi/issues/719#issuecomment-484205696
 - DietPi-Config | Resolved an issue where proxy settings would not be correct after a reboot. Many thanks to @stephantual for reporting this!: https://github.com/MichaIng/DietPi/issues/2704
 - DietPi-Update | Resolved an issue where on older images first run update didn't finalise as intended, leading to several first run setup issues, depending on the image age. The fix has been applied outside of the releases since only the online part of the updater is affected: https://github.com/MichaIng/DietPi/pull/2684
diff --git a/PREP_SYSTEM_FOR_DIETPI.sh b/PREP_SYSTEM_FOR_DIETPI.sh
index 3eaf44825b..cc99350f0f 100644
--- a/PREP_SYSTEM_FOR_DIETPI.sh
+++ b/PREP_SYSTEM_FOR_DIETPI.sh
@@ -60,6 +60,21 @@
 	# - OMV: https://dietpi.com/phpbb/viewtopic.php?f=11&t=2772&p=10646#p10594
 	[[ -f /etc/apt/sources.list.d/openmediavault.list ]] && rm /etc/apt/sources.list.d/openmediavault.list
 
+	# Fixing sources.list due to Debian dropped Jessie support: https://github.com/MichaIng/DietPi/issues/2665
+	if grep -qi 'jessie' /etc/os-release && ! grep -qi 'raspbian' /etc/os-release; then
+
+		if [[ $(uname -m) == 'aarch64' ]]; then
+
+			echo 'deb http://archive.debian.org/debian/ main contrib non-free' > /etc/apt/sources.list
+
+		else
+
+			sed -Ei '/jessie(\/updates|-backports|-updates)/d' /etc/apt/sources.list
+
+		fi
+
+	fi
+
 	apt-get clean
 	apt-get update
 	for i in "${a_MIN_APT_PREREQS[@]}"
diff --git a/dietpi/dietpi-config b/dietpi/dietpi-config
index 7d72dee29d..80badea093 100644
--- a/dietpi/dietpi-config
+++ b/dietpi/dietpi-config
@@ -4410,6 +4410,17 @@ Additional benchmarks:
 
 				'APT Mirror')
 
+					# Jessie ARMv8: https://github.com/MichaIng/DietPi/issues/2665#issuecomment-477348864
+					if (( $G_HW_ARCH == 3 && $G_DISTRO < 4 )); then
+
+						G_WHIP_MSG '[INFO] Debian has dropped the Jessie ARMv8 branch from the official APT repository.\n
+Related packages are now available only from the archive: http://archive.debian.org/debian/\n
+This has been applied to your APT sources.list during DietPi update to v6.23 and it cannot be changed.\n
+Aborting...'
+						return
+
+					fi
+
 					# Create Menu List for Whiptail
 					G_WHIP_MENU_ARRAY=('Custom' ': Manually enter APT mirror')
 
diff --git a/dietpi/func/dietpi-set_software b/dietpi/func/dietpi-set_software
index b409c056a7..edca9157ee 100644
--- a/dietpi/func/dietpi-set_software
+++ b/dietpi/func/dietpi-set_software
@@ -106,8 +106,13 @@ $FP_SCRIPT	setpermissions		Applies required filesystem permissions to DietPi spe
 
 		if [[ $INPUT_MODE_VALUE ]]; then
 
+			# - Jessie ARMv8: https://github.com/MichaIng/DietPi/issues/2665#issuecomment-477348864
+			if (( $G_HW_ARCH == 3 && $G_DISTRO < 4 )); then
+
+				INPUT_MODE_VALUE='http://archive.debian.org/debian/'
+
 			# - Set defaults?
-			if [[ $INPUT_MODE_VALUE == 'default' ]]; then
+			elif [[ $INPUT_MODE_VALUE == 'default' ]]; then
 
 				if (( $G_HW_MODEL < 10 )); then
 
@@ -121,17 +126,16 @@ $FP_SCRIPT	setpermissions		Applies required filesystem permissions to DietPi spe
 
 			fi
 
-			# - Set raspbian
+			# - Set Raspbian
 			if (( $G_HW_MODEL < 10 )); then
 
 				echo "deb $INPUT_MODE_VALUE $G_DISTRO_NAME main contrib non-free rpi" > /etc/apt/sources.list
-
 				echo "deb https://archive.raspberrypi.org/debian/ $G_DISTRO_NAME main ui" > /etc/apt/sources.list.d/raspi.list
 
 				#	Update dietpi.txt entry
 				G_CONFIG_INJECT 'CONFIG_APT_RASPBIAN_MIRROR=' "CONFIG_APT_RASPBIAN_MIRROR=$INPUT_MODE_VALUE" /DietPi/dietpi.txt
 
-			# - Set debian
+			# - Set Debian
 			else
 
 				cat << _EOF_ > /etc/apt/sources.list
@@ -141,13 +145,10 @@ deb https://deb.debian.org/debian-security/ $G_DISTRO_NAME/updates main contrib
 deb $INPUT_MODE_VALUE $G_DISTRO_NAME-backports main contrib non-free
 _EOF_
 
-				#	Jessie, switch deb.debian.org to http: https://github.com/MichaIng/DietPi/issues/1285#issuecomment-351830101
+				#	Jessie: https://github.com/MichaIng/DietPi/issues/2665#issuecomment-477348864
 				if (( $G_DISTRO < 4 )); then
 
-					sed -i 's/https:/http:/g' /etc/apt/sources.list
-
-					# - ARM64 packages no longer available: https://github.com/MichaIng/DietPi/issues/1915
-					(( $G_HW_ARCH == 3 )) && sed -i '/debian-security/d' /etc/apt/sources.list
+					echo "deb $INPUT_MODE_VALUE $G_DISTRO_NAME main contrib non-free" > /etc/apt/sources.list
 
 				#	Buster, remove backports: https://github.com/MichaIng/DietPi/issues/1285#issuecomment-351830101
 				elif (( $G_DISTRO > 4 )); then
diff --git a/dietpi/pre-patch_file b/dietpi/pre-patch_file
index e3147ef440..3713371d3b 100644
--- a/dietpi/pre-patch_file
+++ b/dietpi/pre-patch_file
@@ -74,6 +74,7 @@
 		#-------------------------------------------------------------------------------
 		# Pre-patch 4: https://github.com/MichaIng/DietPi/issues/2656
 		# Pre-patch 5: Add new G_CHECK_URL dietpi.txt settings
+		# Pre-patch 6: https://github.com/MichaIng/DietPi/pull/2728
 		if (( $G_DIETPI_VERSION_SUB < 23 )); then
 
 			if [[ -f '/etc/apt/preferences.d/dietpi-wireguard' ]]; then
@@ -87,6 +88,21 @@ Package: wireguard wireguard-dkms wireguard-tools\nPin: release n=sid\nPin-Prior
 			grep -q 'CONFIG_G_CHECK_URL_TIMEOUT' /DietPi/dietpi.txt || echo 'CONFIG_G_CHECK_URL_TIMEOUT=5' >> /DietPi/dietpi.txt || { EXIT_CODE=5; break; }
 			grep -q 'CONFIG_G_CHECK_URL_ATTEMPTS' /DietPi/dietpi.txt || echo 'CONFIG_G_CHECK_URL_ATTEMPTS=3' >> /DietPi/dietpi.txt || { EXIT_CODE=5; break; }
 
+			if (( $(sed -n 1p /DietPi/dietpi/.hw_model) > 9 )) && grep -qi 'jessie' /etc/os-release; then
+
+				echo -e '\e[90m[\e[0m INFO \e[90m]\e[0m Pre-patch 6 | Applying changes to APT sources.list since Debian dropped support for Jessie systems'
+				if [[ $(uname -m) == 'aarch64' ]]; then
+
+					echo 'deb http://archive.debian.org/debian/ main contrib non-free' > /etc/apt/sources.list || { EXIT_CODE=6; break; }
+
+				else
+
+					sed -Ei '/(debian-security|jessie-backports|jessie-updates)/d' /etc/apt/sources.list || { EXIT_CODE=6; break; }
+
+				fi
+
+			fi
+
 		fi
 		#-------------------------------------------------------------------------------
 		# Finished