diff --git a/hscontrol/app.go b/hscontrol/app.go
index ed0da82a..ac63b472 100644
--- a/hscontrol/app.go
+++ b/hscontrol/app.go
@@ -509,6 +509,10 @@ func (h *Headscale) createRouter(grpcMux *grpcRuntime.ServeMux) *chi.Mux {
 		r.Use(h.httpAuthenticationMiddleware)
 		r.HandleFunc("/v1/*", grpcMux.ServeHTTP)
 	})
+	// Ping response endpoint: receives HEAD from clients responding
+	// to a PingRequest. The unguessable ping ID serves as authentication.
+	r.Head("/machine/ping-response", h.PingResponseHandler)
+
 	r.Get("/favicon.ico", FaviconHandler)
 	r.Get("/", BlankHandler)
 
diff --git a/hscontrol/debug.go b/hscontrol/debug.go
index 64c8e0d5..096ea25b 100644
--- a/hscontrol/debug.go
+++ b/hscontrol/debug.go
@@ -1,16 +1,21 @@
 package hscontrol
 
 import (
+	"context"
 	"encoding/json"
 	"fmt"
 	"net"
 	"net/http"
 	"net/netip"
 	"strings"
+	"time"
 
 	"github.com/arl/statsviz"
+	"github.com/juanfont/headscale/hscontrol/templates"
 	"github.com/juanfont/headscale/hscontrol/types"
+	"github.com/juanfont/headscale/hscontrol/types/change"
 	"github.com/prometheus/client_golang/prometheus/promhttp"
+	"tailscale.com/tailcfg"
 	"tailscale.com/tsweb"
 )
 
@@ -324,6 +329,42 @@ func (h *Headscale) debugHTTPServer() *http.Server {
 		}
 	}))
 
+	// Ping endpoint: sends a PingRequest to a node and waits for it to respond.
+	// Supports POST (form submit) and GET with ?node= (clickable quick-ping links).
+	debug.Handle("ping", "Ping a node to check connectivity", http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		var (
+			query  string
+			result *templates.PingResult
+		)
+
+		switch r.Method {
+		case http.MethodPost:
+			r.Body = http.MaxBytesReader(w, r.Body, 4096) //nolint:mnd
+
+			err := r.ParseForm()
+			if err != nil {
+				http.Error(w, "bad form data", http.StatusBadRequest)
+				return
+			}
+
+			query = r.FormValue("node")
+			result = h.doPing(r.Context(), query)
+		case http.MethodGet:
+			// Support ?node= for auto-ping links from other debug pages.
+			if q := r.URL.Query().Get("node"); q != "" {
+				query = q
+				result = h.doPing(r.Context(), query)
+			}
+		}
+
+		nodes := h.connectedNodesList()
+
+		w.Header().Set("Content-Type", "text/html; charset=utf-8")
+		w.WriteHeader(http.StatusOK)
+		//nolint:gosec // elem-go auto-escapes all attribute values; no XSS risk.
+		_, _ = w.Write([]byte(templates.PingPage(query, result, nodes).Render()))
+	}))
+
 	// statsviz.Register would mount handlers directly on the raw mux,
 	// bypassing the access gate. Build the server by hand and wrap
 	// each handler with protectedDebugHandler.
@@ -436,3 +477,94 @@ func (h *Headscale) debugBatcherJSON() DebugBatcherInfo {
 
 	return info
 }
+
+// connectedNodesList returns a list of connected nodes for the ping page.
+func (h *Headscale) connectedNodesList() []templates.ConnectedNode {
+	debugInfo := h.mapBatcher.Debug()
+
+	var nodes []templates.ConnectedNode
+
+	for nodeID, info := range debugInfo {
+		if !info.Connected {
+			continue
+		}
+
+		nv, ok := h.state.GetNodeByID(nodeID)
+		if !ok {
+			continue
+		}
+
+		cn := templates.ConnectedNode{
+			ID:       nodeID,
+			Hostname: nv.Hostname(),
+		}
+
+		for _, ip := range nv.IPs() {
+			cn.IPs = append(cn.IPs, ip.String())
+		}
+
+		nodes = append(nodes, cn)
+	}
+
+	return nodes
+}
+
+const pingTimeout = 30 * time.Second
+
+// doPing sends a PingRequest to the node identified by query and waits for a response.
+func (h *Headscale) doPing(ctx context.Context, query string) *templates.PingResult {
+	if query == "" {
+		return &templates.PingResult{
+			Status:  "error",
+			Message: "No node specified.",
+		}
+	}
+
+	node, ok := h.state.ResolveNode(query)
+	if !ok {
+		return &templates.PingResult{
+			Status:  "error",
+			Message: fmt.Sprintf("Node %q not found.", query),
+		}
+	}
+
+	nodeID := node.ID()
+
+	if !h.mapBatcher.IsConnected(nodeID) {
+		return &templates.PingResult{
+			Status:  "error",
+			NodeID:  nodeID,
+			Message: fmt.Sprintf("Node %d is not connected.", nodeID),
+		}
+	}
+
+	pingID, responseCh := h.state.RegisterPing(nodeID)
+	defer h.state.CancelPing(pingID)
+
+	callbackURL := h.cfg.ServerURL + "/machine/ping-response?id=" + pingID
+	h.Change(change.PingNode(nodeID, &tailcfg.PingRequest{
+		URL: callbackURL,
+		Log: true,
+	}))
+
+	select {
+	case latency := <-responseCh:
+		return &templates.PingResult{
+			Status:  "ok",
+			Latency: latency,
+			NodeID:  nodeID,
+		}
+	case <-time.After(pingTimeout):
+		return &templates.PingResult{
+			Status:  "timeout",
+			NodeID:  nodeID,
+			Message: fmt.Sprintf("No response after %s.", pingTimeout),
+		}
+	case <-ctx.Done():
+		return &templates.PingResult{
+			Status:  "error",
+			NodeID:  nodeID,
+			Message: "Request cancelled.",
+		}
+	}
+}
diff --git a/hscontrol/mapper/builder.go b/hscontrol/mapper/builder.go
index 0410e16a..2a3add8e 100644
--- a/hscontrol/mapper/builder.go
+++ b/hscontrol/mapper/builder.go
@@ -277,6 +277,12 @@ func (b *MapResponseBuilder) buildTailPeers(peers views.Slice[types.NodeView]) (
 	return tailPeers, nil
 }
 
+// WithPingRequest adds a PingRequest to the response.
+func (b *MapResponseBuilder) WithPingRequest(pr *tailcfg.PingRequest) *MapResponseBuilder {
+	b.resp.PingRequest = pr
+	return b
+}
+
 // WithPeerChangedPatch adds peer change patches.
 func (b *MapResponseBuilder) WithPeerChangedPatch(changes []*tailcfg.PeerChange) *MapResponseBuilder {
 	b.resp.PeersChangedPatch = changes
diff --git a/hscontrol/mapper/mapper.go b/hscontrol/mapper/mapper.go
index 0aba4175..ab2399a5 100644
--- a/hscontrol/mapper/mapper.go
+++ b/hscontrol/mapper/mapper.go
@@ -308,6 +308,10 @@ func (m *mapper) buildFromChange(
 		builder.WithPeerChangedPatch(resp.PeerPatches)
 	}
 
+	if resp.PingRequest != nil {
+		builder.WithPingRequest(resp.PingRequest)
+	}
+
 	return builder.Build()
 }
 
diff --git a/hscontrol/noise.go b/hscontrol/noise.go
index 12d9adf7..0a84d96f 100644
--- a/hscontrol/noise.go
+++ b/hscontrol/noise.go
@@ -295,6 +295,26 @@ func (ns *noiseServer) NotImplementedHandler(writer http.ResponseWriter, req *ht
 	http.Error(writer, "Not implemented yet", http.StatusNotImplemented)
 }
 
+// PingResponseHandler handles HEAD requests from clients responding to a
+// PingRequest. The client calls this endpoint to prove connectivity.
+// The unguessable ping ID serves as authentication.
+func (h *Headscale) PingResponseHandler(
+	writer http.ResponseWriter,
+	req *http.Request,
+) {
+	pingID := req.URL.Query().Get("id")
+	if pingID == "" {
+		http.Error(writer, "missing ping ID", http.StatusBadRequest)
+		return
+	}
+
+	if h.state.CompletePing(pingID) {
+		writer.WriteHeader(http.StatusOK)
+	} else {
+		http.Error(writer, "unknown or expired ping", http.StatusNotFound)
+	}
+}
+
 func urlParam[T any](req *http.Request, key string) (T, error) {
 	var zero T
 
diff --git a/hscontrol/state/ping.go b/hscontrol/state/ping.go
new file mode 100644
index 00000000..a7e2df30
--- /dev/null
+++ b/hscontrol/state/ping.go
@@ -0,0 +1,97 @@
+package state
+
+import (
+	"sync"
+	"time"
+
+	"github.com/juanfont/headscale/hscontrol/types"
+	"github.com/juanfont/headscale/hscontrol/util"
+)
+
+const pingIDLength = 16
+
+// pingTracker manages pending ping requests and their response channels.
+// It correlates outgoing PingRequests with incoming HEAD callbacks.
+type pingTracker struct {
+	mu      sync.Mutex
+	pending map[string]*pendingPing
+}
+
+type pendingPing struct {
+	nodeID     types.NodeID
+	startTime  time.Time
+	responseCh chan time.Duration
+}
+
+func newPingTracker() *pingTracker {
+	return &pingTracker{
+		pending: make(map[string]*pendingPing),
+	}
+}
+
+// register creates a new pending ping and returns a unique ping ID
+// and a channel that will receive the round-trip latency when the
+// ping response arrives.
+func (pt *pingTracker) register(nodeID types.NodeID) (string, <-chan time.Duration) {
+	pingID, _ := util.GenerateRandomStringDNSSafe(pingIDLength)
+	ch := make(chan time.Duration, 1)
+
+	pt.mu.Lock()
+	pt.pending[pingID] = &pendingPing{
+		nodeID:     nodeID,
+		startTime:  time.Now(),
+		responseCh: ch,
+	}
+	pt.mu.Unlock()
+
+	return pingID, ch
+}
+
+// complete signals that a ping response was received.
+// It sends the measured latency on the response channel and returns true.
+// Returns false if the pingID is unknown (already completed, cancelled, or expired).
+func (pt *pingTracker) complete(pingID string) bool {
+	pt.mu.Lock()
+
+	pp, ok := pt.pending[pingID]
+	if ok {
+		delete(pt.pending, pingID)
+	}
+	pt.mu.Unlock()
+
+	if ok {
+		pp.responseCh <- time.Since(pp.startTime)
+
+		close(pp.responseCh)
+
+		return true
+	}
+
+	return false
+}
+
+// cancel removes a pending ping without completing it.
+// Used for cleanup when the caller times out or disconnects.
+func (pt *pingTracker) cancel(pingID string) {
+	pt.mu.Lock()
+	delete(pt.pending, pingID)
+	pt.mu.Unlock()
+}
+
+// RegisterPing creates a pending ping for the given node and returns
+// a unique ping ID and a channel that receives the round-trip latency
+// when the response arrives.
+func (s *State) RegisterPing(nodeID types.NodeID) (string, <-chan time.Duration) {
+	return s.pings.register(nodeID)
+}
+
+// CompletePing signals that a ping response was received for the given ID.
+// Returns true if the ping was found and completed, false otherwise.
+func (s *State) CompletePing(pingID string) bool {
+	return s.pings.complete(pingID)
+}
+
+// CancelPing removes a pending ping without completing it.
+func (s *State) CancelPing(pingID string) {
+	s.pings.cancel(pingID)
+}
diff --git a/hscontrol/state/state.go b/hscontrol/state/state.go
index 9053735e..af9e984c 100644
--- a/hscontrol/state/state.go
+++ b/hscontrol/state/state.go
@@ -146,6 +146,9 @@ type State struct {
 	// only proceeds when the generation it carries matches the latest.
 	connectGen sync.Map // types.NodeID → *atomic.Uint64
 
+	// pings tracks pending ping requests and their response channels.
+	pings *pingTracker
+
 	// sshCheckAuth tracks when source nodes last completed SSH check auth.
 	//
 	// For rules without explicit checkPeriod (default 12h), auth covers any
@@ -256,6 +259,7 @@ func NewState(cfg *types.Config) (*State, error) {
 		authCache:     authCache,
 		primaryRoutes: routes.New(),
 		nodeStore:     nodeStore,
+		pings:         newPingTracker(),
 
 		sshCheckAuth: make(map[sshCheckPair]time.Time),
 	}, nil
@@ -699,6 +703,37 @@ func (s *State) GetNodeByMachineKey(machineKey key.MachinePublic, userID types.U
 	return s.nodeStore.GetNodeByMachineKey(machineKey, userID)
 }
 
+// ResolveNode looks up a node by numeric ID, IPv4/IPv6 address, hostname, or given name.
+// It tries ID first, then IP, then name matching.
+func (s *State) ResolveNode(query string) (types.NodeView, bool) {
+	// Try numeric ID first.
+	id, idErr := types.ParseNodeID(query)
+	if idErr == nil {
+		return s.GetNodeByID(id)
+	}
+
+	// Try IP address.
+	addr, addrErr := netip.ParseAddr(query)
+	if addrErr == nil {
+		for _, n := range s.ListNodes().All() {
+			if slices.Contains(n.IPs(), addr) {
+				return n, true
+			}
+		}
+
+		return types.NodeView{}, false
+	}
+
+	// Try hostname / given name.
+	for _, n := range s.ListNodes().All() {
+		if n.Hostname() == query || n.GivenName() == query {
+			return n, true
+		}
+	}
+
+	return types.NodeView{}, false
+}
+
 // ListNodes retrieves specific nodes by ID, or all nodes if no IDs provided.
 func (s *State) ListNodes(nodeIDs ...types.NodeID) views.Slice[types.NodeView] {
 	if len(nodeIDs) == 0 {
diff --git a/hscontrol/templates/ping.go b/hscontrol/templates/ping.go
new file mode 100644
index 00000000..02121455
--- /dev/null
+++ b/hscontrol/templates/ping.go
@@ -0,0 +1,152 @@
+package templates
+
+import (
+	"fmt"
+	"strings"
+	"time"
+
+	elem "github.com/chasefleming/elem-go"
+	"github.com/chasefleming/elem-go/attrs"
+	"github.com/chasefleming/elem-go/styles"
+	"github.com/juanfont/headscale/hscontrol/types"
+)
+
+// PingResult contains the outcome of a ping request.
+type PingResult struct {
+	// Status is "ok", "timeout", or "error".
+	Status string
+
+	// Latency is the round-trip time (only meaningful when Status is "ok").
+	Latency time.Duration
+
+	// NodeID is the ID of the pinged node.
+	NodeID types.NodeID
+
+	// Message is a human-readable description of the result.
+	Message string
+}
+
+// ConnectedNode is a node currently connected to the batcher,
+// displayed as a quick-ping link on the debug ping page.
+type ConnectedNode struct {
+	ID       types.NodeID
+	Hostname string
+	IPs      []string
+}
+
+// PingPage renders the /debug/ping page with a form, optional result,
+// and a list of connected nodes as quick-ping links.
+func PingPage(query string, result *PingResult, nodes []ConnectedNode) *elem.Element {
+	children := []elem.Node{
+		headscaleLogo(),
+		H1(elem.Text("Ping Node")),
+		P(elem.Text("Check if a connected node responds to a PingRequest.")),
+		pingForm(query),
+	}
+
+	if result != nil {
+		children = append(children, pingResult(result))
+	}
+
+	if len(nodes) > 0 {
+		children = append(children, connectedNodeList(nodes))
+	}
+
+	children = append(children, pageFooter())
+
+	return HtmlStructure(
+		elem.Title(nil, elem.Text("Ping Node - Headscale")),
+		mdTypesetBody(children...),
+	)
+}
+
+func pingForm(query string) *elem.Element {
+	inputStyle := styles.Props{
+		styles.Padding:      spaceS,
+		styles.Border:       "1px solid " + colorBorderMedium,
+		styles.BorderRadius: "0.25rem",
+		styles.FontSize:     fontSizeBase,
+		styles.FontFamily:   fontFamilySystem,
+		styles.Width:        "280px",
+	}
+
+	buttonStyle := styles.Props{
+		styles.Padding:         spaceS + " " + spaceM,
+		styles.BackgroundColor: colorPrimaryAccent,
+		styles.Color:           "#ffffff",
+		styles.Border:          "none",
+		styles.BorderRadius:    "0.25rem",
+		styles.FontSize:        fontSizeBase,
+		styles.FontFamily:      fontFamilySystem,
+		"cursor":               "pointer",
+	}
+
+	return elem.Form(attrs.Props{
+		attrs.Method: "POST",
+		attrs.Action: "/debug/ping",
+		attrs.Style: styles.Props{
+			styles.Display:    "flex",
+			styles.Gap:        spaceS,
+			styles.AlignItems: "center",
+			styles.MarginTop:  spaceM,
+		}.ToInline(),
+	},
+		elem.Input(attrs.Props{
+			attrs.Type:        "text",
+			attrs.Name:        "node",
+			attrs.Value:       query,
+			attrs.Placeholder: "Node ID, IP, or hostname",
+			attrs.Autofocus:   "true",
+			attrs.Style:       inputStyle.ToInline(),
+		}),
+		elem.Button(attrs.Props{
+			attrs.Type:  "submit",
+			attrs.Style: buttonStyle.ToInline(),
+		}, elem.Text("Ping")),
+	)
+}
+
+func connectedNodeList(nodes []ConnectedNode) *elem.Element {
+	items := make([]elem.Node, 0, len(nodes))
+
+	for _, n := range nodes {
+		label := fmt.Sprintf("%s (ID: %d, %s)", n.Hostname, n.ID, strings.Join(n.IPs, ", "))
+		href := fmt.Sprintf("/debug/ping?node=%d", n.ID)
+
+		items = append(items, elem.Li(nil,
+			elem.A(attrs.Props{
+				attrs.Href: href,
+				attrs.Style: styles.Props{
+					styles.Color: colorPrimaryAccent,
+				}.ToInline(),
+			}, elem.Text(label)),
+		))
+	}
+
+	return elem.Div(attrs.Props{
+		attrs.Style: styles.Props{
+			styles.MarginTop: spaceL,
+		}.ToInline(),
+	},
+		H2(elem.Text("Connected Nodes")),
+		elem.Ul(nil, items...),
+	)
+}
+
+func pingResult(result *PingResult) *elem.Element {
+	switch result.Status {
+	case "ok":
+		return successBox(
+			"Pong",
+			elem.Text(fmt.Sprintf("Node %d responded in %s",
+				result.NodeID, result.Latency.Round(time.Millisecond))),
+		)
+	case "timeout":
+		return warningBox(
+			"Timeout",
+			fmt.Sprintf("Node %d did not respond. %s", result.NodeID, result.Message),
+		)
+	default:
+		return warningBox("Error", result.Message)
+	}
+}
diff --git a/hscontrol/types/change/change.go b/hscontrol/types/change/change.go
index 7014a6a8..a1f1f8c4 100644
--- a/hscontrol/types/change/change.go
+++ b/hscontrol/types/change/change.go
@@ -39,6 +39,11 @@ type Change struct {
 	// must be computed at runtime per-node. Used for policy changes
 	// where each node may have different peer visibility.
 	RequiresRuntimePeerComputation bool
+
+	// PingRequest, if non-nil, is a ping request to send to the node.
+	// Used by the debug ping endpoint to verify node connectivity.
+	// PingRequest is always targeted to a specific node via TargetNode.
+	PingRequest *tailcfg.PingRequest
 }
 
 // boolFieldNames returns all boolean field names for exhaustive testing.
@@ -93,6 +98,11 @@ func (r Change) Merge(other Change) Change {
 		merged.TargetNode = other.TargetNode
 	}
 
+	// Preserve PingRequest (first wins).
+	if merged.PingRequest == nil {
+		merged.PingRequest = other.PingRequest
+	}
+
 	if r.Reason != "" && other.Reason != "" && r.Reason != other.Reason {
 		merged.Reason = r.Reason + "; " + other.Reason
 	} else if other.Reason != "" {
@@ -112,6 +122,10 @@ func (r Change) IsEmpty() bool {
 		return false
 	}
 
+	if r.PingRequest != nil {
+		return false
+	}
+
 	return len(r.PeersChanged) == 0 &&
 		len(r.PeersRemoved) == 0 &&
 		len(r.PeerPatches) == 0
@@ -168,6 +182,10 @@ func (r Change) Type() string {
 		return "config"
 	}
 
+	if r.PingRequest != nil {
+		return "ping"
+	}
+
 	return "unknown"
 }
 
@@ -454,6 +472,16 @@ func UserRemoved() Change {
 	return c
 }
 
+// PingNode creates a Change that sends a PingRequest to a specific node.
+// The node will respond to the PingRequest URL to prove connectivity.
+func PingNode(nodeID types.NodeID, pr *tailcfg.PingRequest) Change {
+	return Change{
+		Reason:      "ping node",
+		TargetNode:  nodeID,
+		PingRequest: pr,
+	}
+}
+
 // ExtraRecords returns a Change for when DNS extra records change.
 func ExtraRecords() Change {
 	c := DNSConfig()