diff --git a/README.md b/README.md
index 211d615..113ac29 100644
--- a/README.md
+++ b/README.md
@@ -111,11 +111,14 @@ omarchy-send --to "Strong Onion" --message "hi" --send-pin 2468   # if the peer
 ```
 
 The target is matched against the peer's display name, case-insensitively. The
-command discovers the peer over multicast (waiting up to `--wait`, default 15s),
-sends the message, prints a one-line result, and exits non-zero if the peer
-isn't found or the send fails. It starts discovery only — not the receiver — so
-it's safe to run while another `omarchy-send` instance is up. Both `--to` and
-`--message` are required; file sending stays in the TUI for now.
+command discovers the peer over multicast and, like the TUI, directly probes
+your known peers and online Tailscale peers (waiting up to `--wait`, default
+15s) — so a remote box added with `+` in the TUI, or any tailnet peer, is a
+valid `--to` target from a script too. It sends the message, prints a one-line
+result, and exits non-zero if the peer isn't found or the send fails. It starts
+discovery only — not the receiver — so it's safe to run while another
+`omarchy-send` instance is up. Both `--to` and `--message` are required; file
+sending stays in the TUI for now.
 
 ### Sending files
 
diff --git a/cmd/omarchy-send/main.go b/cmd/omarchy-send/main.go
index 84f6852..f01a59b 100644
--- a/cmd/omarchy-send/main.go
+++ b/cmd/omarchy-send/main.go
@@ -337,6 +337,11 @@ func runHeadlessSend(cfg config.Config, target, message, sendPIN string, wait ti
 	}
 	disc.Announce() // solicit replies immediately rather than waiting a tick
 
+	// Multicast can't cross subnets or the tailnet, so also probe known peers
+	// and online Tailscale peers directly — same as the TUI's device list.
+	rem := &remotes{hosts: cfg.KnownPeers}
+	go watchRemotes(ctx, disc, rem)
+
 	want := strings.TrimSpace(target)
 	fmt.Fprintf(os.Stderr, "Looking for %q on the network (up to %s)…\n", want, wait)
 
@@ -353,7 +358,7 @@ func runHeadlessSend(cfg config.Config, target, message, sendPIN string, wait ti
 				fmt.Fprintf(os.Stderr, "  - %q (%s)\n", p.Info.Alias, p.IP)
 			}
 		} else {
-			fmt.Fprintln(os.Stderr, "No peers were seen at all — check you're on the same LAN and the target is running omarchy-send / LocalSend.")
+			fmt.Fprintln(os.Stderr, "No peers were seen at all — check the target is running omarchy-send / LocalSend on the same LAN, or is reachable as a known peer / over Tailscale.")
 		}
 		return 1
 	}
diff --git a/internal/discovery/probe_test.go b/internal/discovery/probe_test.go
index 8fa81aa..d7e239b 100644
--- a/internal/discovery/probe_test.go
+++ b/internal/discovery/probe_test.go
@@ -7,6 +7,7 @@ import (
 	"net/http/httptest"
 	"strings"
 	"testing"
+	"time"
 
 	"omarchy-send/internal/protocol"
 )
@@ -46,6 +47,44 @@ func TestProbeRegistersPeer(t *testing.T) {
 	}
 }
 
+// TestFindPeerViaProbe covers the headless-send path for remote peers: a peer
+// that multicast can't see (here: only reachable by unicast Probe) must still
+// satisfy a FindPeer that is already waiting — Probe → NotePeer → PeerFound.
+func TestFindPeerViaProbe(t *testing.T) {
+	peerInfo := protocol.DeviceInfo{Alias: "titan-box", Fingerprint: "titan-fp", Port: 53317, Protocol: "http"}
+	mux := http.NewServeMux()
+	mux.HandleFunc("/api/localsend/v2/register", func(w http.ResponseWriter, r *http.Request) {
+		_ = json.NewEncoder(w).Encode(peerInfo)
+	})
+	srv := httptest.NewServer(mux)
+	defer srv.Close()
+	host := strings.TrimPrefix(srv.URL, "http://")
+
+	d := New(protocol.DeviceInfo{Fingerprint: "self-fp", Alias: "Self"})
+
+	// Probe concurrently, like watchRemotes does while FindPeer waits.
+	go func() {
+		if err := d.Probe(context.Background(), host); err != nil {
+			t.Errorf("Probe failed: %v", err)
+		}
+	}()
+
+	ctx, cancel := context.WithTimeout(context.Background(), 2*time.Second)
+	defer cancel()
+	got, err := d.FindPeer(ctx, func(p Peer) bool {
+		return strings.EqualFold(strings.TrimSpace(p.Info.Alias), "titan-box")
+	})
+	if err != nil {
+		t.Fatalf("FindPeer did not see the probed peer: %v", err)
+	}
+	if got.Info.Fingerprint != "titan-fp" {
+		t.Errorf("fingerprint = %q, want titan-fp", got.Info.Fingerprint)
+	}
+	if wantIP := strings.Split(host, ":")[0]; got.IP != wantIP {
+		t.Errorf("peer IP = %q, want %q (the host probed)", got.IP, wantIP)
+	}
+}
+
 func TestProbeUnreachableErrors(t *testing.T) {
 	d := New(protocol.DeviceInfo{Fingerprint: "self-fp"})
 	// 127.0.0.1:1 — nothing listening; both https and http should fail fast.