diff --git a/util/flash_disk.gdb b/util/flash_disk.gdb
new file mode 100644
index 00000000..0dabdda6
--- /dev/null
+++ b/util/flash_disk.gdb
@@ -0,0 +1,23 @@
+# Copyright 2024 ETH Zurich and University of Bologna.
+# Licensed under the Apache License, Version 2.0, see LICENSE for details.
+# SPDX-License-Identifier: Apache-2.0
+#
+# Cheshire disk flashing script for use with GDB.
+
+target extended-remote localhost:3333
+
+# Load flashing program
+load sw/boot/flash.spm.elf
+
+# Load disk image to DRAM
+eval "restore %s binary 0x80000000", $img
+
+# Write flash parameters to scratch regs
+set *0x03000000=$target
+set *0x03000004=0x80000000
+set *0x03000008=$offs
+set *0x0300000c=$len
+
+# Launch payload and quit after return
+continue
+quit
diff --git a/util/flash_disk.sh b/util/flash_disk.sh
new file mode 100755
index 00000000..78fd4cc2
--- /dev/null
+++ b/util/flash_disk.sh
@@ -0,0 +1,33 @@
+#! /usr/bin/env bash
+#
+# Copyright 2024 ETH Zurich and University of Bologna.
+# Licensed under the Apache License, Version 2.0, see LICENSE for details.
+# SPDX-License-Identifier: Apache-2.0
+#
+# Cheshire disk flashing script invoking OpenOCD and GDB.
+#
+# Arguments:
+# $1: target board
+# $2: target disk
+# $3: (optional): disk image
+# $4: (optional): copy length
+# $5: (optional): copy offset
+
+set -e
+
+# Determine the image name and size
+img=${3:-sw/boot/linux.${1}.gpt.bin}
+# Ensure the image exists and determine rounded-up size
+len=${4:-$(stat -c%s ${img})}
+len=$((len/512+1))
+
+# Run OpenOCD and GDB
+openocd -f util/openocd.${1}.tcl &
+sleep 2
+riscv64-unknown-elf-gdb --batch \
+    -ex "set \$target = ${2:-1}" \
+    -ex "set \$img = \"${img}\"" \
+    -ex "set \$len = ${len}" \
+    -ex "set \$offs = ${5:-0}" \
+    -ex "source util/flash_disk.gdb"
+wait
diff --git a/util/openocd.common.tcl b/util/openocd.common.tcl
index 7474f015..ecba985c 100644
--- a/util/openocd.common.tcl
+++ b/util/openocd.common.tcl
@@ -23,10 +23,16 @@ riscv set_command_timeout_sec 120
 
 riscv set_prefer_sba off
 
+# Exit when debugger detaches
+$_TARGETNAME configure -event gdb-detach {
+    echo "GDB detached; ending debugging session."
+    shutdown
+}
+
 # Try enabling address translation (only works for newer versions)
 if { [catch {riscv set_enable_virtual on} ] } {
     echo "Warning: This version of OpenOCD does not support address translation. To debug on virtual addresses, please update to the latest version." }
 
 init
 halt
-echo "Ready for Remote Connections"
+echo "Ready for Remote Connections."