diff --git a/download-packages.sh b/download-packages.sh
index c9b47c1..d698934 100755
--- a/download-packages.sh
+++ b/download-packages.sh
@@ -29,6 +29,7 @@ PLAYBOOK_PACKAGES=(
     p7zip-full
     grub-efi-amd64-bin
     grub-common
+    conntrack
 )
 
 # Packages installed during autoinstall late-commands (NetworkManager, WiFi, etc.)
diff --git a/playbook/pxe-server-helpers/99-pxe-conntrack.conf b/playbook/pxe-server-helpers/99-pxe-conntrack.conf
new file mode 100644
index 0000000..e5285db
--- /dev/null
+++ b/playbook/pxe-server-helpers/99-pxe-conntrack.conf
@@ -0,0 +1,13 @@
+# Reduce nf_conntrack TCP timeouts so stale SMB sessions from rebooted WinPE
+# clients age out in minutes instead of days. Real active sessions stay
+# alive via keepalive traffic refreshing the conntrack timer. Defaults
+# (432000s = 5 days for ESTABLISHED) are designed for long-lived enterprise
+# TCP flows, not the short bursty connections PXE imaging creates.
+#
+# Paired with Samba's keepalive=30 + SO_KEEPALIVE (see smb.conf) the
+# combination is: dead sessions cleaned up in ~1 hour max, active sessions
+# never ageing out because every keepalive packet refreshes the timer.
+net.netfilter.nf_conntrack_tcp_timeout_established = 3600
+net.netfilter.nf_conntrack_tcp_timeout_fin_wait    = 30
+net.netfilter.nf_conntrack_tcp_timeout_last_ack    = 30
+net.netfilter.nf_conntrack_tcp_timeout_close_wait  = 30
diff --git a/playbook/pxe-server-helpers/smb-diag.sh b/playbook/pxe-server-helpers/smb-diag.sh
new file mode 100755
index 0000000..0d87e76
--- /dev/null
+++ b/playbook/pxe-server-helpers/smb-diag.sh
@@ -0,0 +1,85 @@
+#!/bin/bash
+# smb-diag.sh - snapshot Samba + kernel network state so a future failure
+# can be diagnosed remotely. Run this on the PXE server BEFORE power-cycling
+# when a WinPE re-image client is getting "cannot connect" errors.
+#
+# Output: /tmp/smb-diag-<timestamp>.log (pastebin-friendly)
+#
+# Captures: smbd processes, open SMB sessions, port 445 TCP sockets,
+#           conntrack, arp, bridge fdb, dnsmasq leases, recent smbd logs.
+
+set -o pipefail
+
+TS=$(date +%Y%m%d-%H%M%S)
+OUT=/tmp/smb-diag-$TS.log
+
+exec > >(tee "$OUT") 2>&1
+
+echo "=============================================================="
+echo "SMB diagnostic snapshot - $(date)"
+echo "=============================================================="
+
+echo
+echo "### uptime / kernel ###"
+uptime
+uname -r
+
+echo
+echo "### interfaces + bridge state ###"
+ip -brief addr
+echo
+bridge link show 2>/dev/null
+echo
+bridge fdb show 2>/dev/null | head -30
+
+echo
+echo "### smbd process tree ###"
+pstree -p $(systemctl show -p MainPID --value smbd 2>/dev/null) 2>/dev/null
+echo
+ps -eo pid,ppid,state,command | grep -E 'smbd|nmbd' | grep -v grep
+
+echo
+echo "### systemctl status ###"
+systemctl is-active smbd nmbd dnsmasq apache2
+
+echo
+echo "### smbstatus ###"
+smbstatus 2>&1 | head -40
+
+echo
+echo "### port 445 sockets ###"
+ss -tnp 2>/dev/null | grep :445
+
+echo
+echo "### conntrack entries for PXE subnet ###"
+if command -v conntrack >/dev/null 2>&1; then
+    conntrack -L 2>&1 | grep -E '10\.9\.100' | head -30
+    echo "total conntrack entries: $(conntrack -C 2>&1)"
+else
+    echo "conntrack tool not installed"
+fi
+
+echo
+echo "### arp / neighbour table for PXE subnet ###"
+ip neigh show 2>/dev/null | grep -E '10\.9\.100|br-pxe'
+
+echo
+echo "### dnsmasq DHCP leases ###"
+cat /var/lib/misc/dnsmasq.leases 2>/dev/null | head -20
+
+echo
+echo "### recent smbd log files ###"
+ls -la /var/log/samba/ 2>/dev/null | head -20
+
+echo
+echo "### recent smbd auth / status errors (all machine logs) ###"
+grep -hE 'NT_STATUS|error|denied' /var/log/samba/log.*.log 2>/dev/null | tail -30
+
+echo
+echo "### last 20 lines of smbd master log ###"
+tail -20 /var/log/samba/log.smbd 2>/dev/null
+
+echo
+echo "=============================================================="
+echo "Snapshot saved to $OUT"
+echo "=============================================================="
diff --git a/playbook/pxe-server-helpers/smb-soft-reset.sh b/playbook/pxe-server-helpers/smb-soft-reset.sh
new file mode 100755
index 0000000..bc3b9d7
--- /dev/null
+++ b/playbook/pxe-server-helpers/smb-soft-reset.sh
@@ -0,0 +1,87 @@
+#!/bin/bash
+# smb-soft-reset.sh - progressive soft recovery for the WinPE re-image
+# "System error 53 has occurred" issue without having to power-cycle the box.
+# Error 53 = network path not found; the TCP connect to :445 never
+# completes. Root cause is almost always stale kernel netfilter conntrack
+# state that systemctl restart smbd doesn't touch. Full reboot clears it;
+# this script tries to do the same without the reboot.
+#
+# Run as root (sudo) when the issue happens. It applies increasingly
+# aggressive fixes and pauses between steps so you can retry the WinPE
+# re-image without closing this shell.
+#
+# Step 1: reload smbd config  (cheapest, may clear cached state)
+# Step 2: restart nmbd         (NetBIOS daemon - separate from smbd)
+# Step 3: restart smbd         (full smbd restart, kills all child sessions)
+# Step 4: kill any leftover smbd child processes that survived restart
+# Step 5: flush conntrack for 10.9.100.0/24 (kernel connection tracking)
+# Step 6: flush ARP / neighbour cache on br-pxe
+# Step 7: drop TCP sockets on port 445 via ss -K
+# Step 8: restart dnsmasq      (DHCP/TFTP state as a last resort before reboot)
+
+set -e
+
+pause() {
+    echo
+    echo "----------------------------------------------------------------"
+    echo "$1"
+    echo "  Try your WinPE re-image NOW. Did it work?"
+    echo "  [Enter] to continue to next step, Ctrl+C to stop."
+    echo "----------------------------------------------------------------"
+    read -r _
+}
+
+if [ "$EUID" -ne 0 ]; then
+    echo "Run as root: sudo $0" >&2
+    exit 1
+fi
+
+echo "=== Step 1/8: reload smbd config ==="
+systemctl reload smbd 2>&1 || true
+pause "Step 1 done"
+
+echo "=== Step 2/8: restart nmbd ==="
+systemctl restart nmbd 2>&1 || true
+pause "Step 2 done"
+
+echo "=== Step 3/8: restart smbd ==="
+systemctl restart smbd 2>&1
+pause "Step 3 done"
+
+echo "=== Step 4/8: kill any leftover smbd children ==="
+# systemctl restart should take care of this with KillMode=control-group,
+# but belt + suspenders since the issue has been surviving restarts.
+pkill -9 -x smbd 2>/dev/null || true
+sleep 1
+systemctl start smbd 2>&1
+pause "Step 4 done"
+
+echo "=== Step 5/8: flush conntrack entries for 10.9.100.0/24 ==="
+if command -v conntrack >/dev/null 2>&1; then
+    conntrack -D -s 10.9.100.0/24 2>&1 || true
+    conntrack -D -d 10.9.100.0/24 2>&1 || true
+else
+    echo "  conntrack tool not installed - skipping (apt install conntrack)"
+fi
+pause "Step 5 done"
+
+echo "=== Step 6/8: flush ARP / neighbour cache on br-pxe ==="
+ip neigh flush dev br-pxe 2>&1 || ip neigh flush all 2>&1 || true
+pause "Step 6 done"
+
+echo "=== Step 7/8: drop tcp sockets on port 445 ==="
+# ss -K requires iproute2 >= 4.11 and CONFIG_INET_DIAG_DESTROY in the kernel.
+# Drops existing TCP connections to port 445 without touching listening socket.
+ss -K dport = 445 2>&1 || echo "  ss -K not supported on this system"
+ss -K sport = 445 2>&1 || true
+pause "Step 7 done"
+
+echo "=== Step 8/8: restart dnsmasq ==="
+systemctl restart dnsmasq 2>&1
+pause "Step 8 done"
+
+echo
+echo "All soft-fix steps exhausted. If the issue is still present, you'll"
+echo "have to power-cycle. Before you do, run /usr/local/sbin/smb-diag.sh"
+echo "and share the /tmp/smb-diag-*.log output so we can pinpoint which"
+echo "kernel state the reboot is actually clearing."
diff --git a/playbook/pxe_server_setup.yml b/playbook/pxe_server_setup.yml
index 17dd309..d2ccdd6 100644
--- a/playbook/pxe_server_setup.yml
+++ b/playbook/pxe_server_setup.yml
@@ -17,6 +17,7 @@
         - cron
         - ansible
         - wimtools
+        - conntrack
       register: pkg_check
       failed_when: false
       changed_when: false
@@ -364,6 +365,23 @@
           wide links = yes
           unix extensions = no
 
+    - name: "Samba SMB session handling for WinPE re-image robustness"
+      blockinfile:
+        path: /etc/samba/smb.conf
+        backup: yes
+        marker: "# {mark} MANAGED - PXE REIMAGE FIX"
+        insertafter: "# END MANAGED - GLOBAL SYMLINKS"
+        block: |
+          # Reduce the chance a WinPE client rebooting mid-imaging leaves a
+          # stale session on the server that blocks its next connection
+          # attempt with "System error 53 network path not found". Combined
+          # with /etc/sysctl.d/99-pxe-conntrack.conf (shorter nf_conntrack
+          # TCP timeouts) this keeps the conntrack + smbd state in sync with
+          # the short-lived flows that PXE imaging produces.
+             socket options = TCP_NODELAY SO_KEEPALIVE IPTOS_LOWDELAY
+             keepalive = 30
+             deadtime = 5
+
     - name: "Configure Samba shares"
       blockinfile:
         path: /etc/samba/smb.conf
@@ -427,6 +445,22 @@
         executable: /bin/bash
       changed_when: false
 
+    - name: "Deploy nf_conntrack TCP timeout sysctl for PXE workload"
+      copy:
+        src: "{{ usb_mount }}/pxe-server-helpers/99-pxe-conntrack.conf"
+        dest: /etc/sysctl.d/99-pxe-conntrack.conf
+        mode: '0644'
+      notify: reload sysctl
+
+    - name: "Deploy SMB diagnostic + soft-reset helper scripts"
+      copy:
+        src: "{{ usb_mount }}/pxe-server-helpers/{{ item }}"
+        dest: "/usr/local/sbin/{{ item }}"
+        mode: '0755'
+      loop:
+        - smb-diag.sh
+        - smb-soft-reset.sh
+
     - name: "Create image-type top-level directories"
       file:
         path: "{{ samba_share }}/{{ item }}"
@@ -784,3 +818,6 @@
   handlers:
     - name: "Apply netplan"
       command: netplan apply
+
+    - name: "reload sysctl"
+      command: sysctl --system