diff --git a/toolsrv/bootstrap.sh b/toolsrv/bootstrap.sh
index cac9aa9..43f3bf3 100644
--- a/toolsrv/bootstrap.sh
+++ b/toolsrv/bootstrap.sh
@@ -1,15 +1,27 @@
 #!/bin/sh
 # Bootstrap script for ollie-remote SSH deployment.
-# Checks for cached binary by hash, downloads if needed, then execs.
+# Checks for cached binaries by hash, downloads if needed, then execs.
 main() {
 set -e
 #
 CACHE_DIR="${XDG_CACHE_HOME:-$HOME/.cache}/ollie/bin"
 CACHE_BIN="$CACHE_DIR/ollie-remote"
 CACHE_HASH="$CACHE_DIR/ollie-remote.hash"
+CACHE_LANDRUN="$CACHE_DIR/landrun"
+CACHE_LANDRUN_HASH="$CACHE_DIR/landrun.hash"
 #
-if [ -x "$CACHE_BIN" ] && [ -f "$CACHE_HASH" ] && [ "$(cat "$CACHE_HASH")" = "@@HASH@@" ]; then
-  echo "OLLIE_LOADER_START {\"need_download\":false}" >&2
+NEED_DOWNLOAD=false
+NEED_LANDRUN=false
+#
+if ! [ -x "$CACHE_BIN" ] || ! [ -f "$CACHE_HASH" ] || [ "$(cat "$CACHE_HASH")" != "@@HASH@@" ]; then
+  NEED_DOWNLOAD=true
+fi
+if ! [ -x "$CACHE_LANDRUN" ] || ! [ -f "$CACHE_LANDRUN_HASH" ] || [ "$(cat "$CACHE_LANDRUN_HASH")" != "@@LANDRUN_HASH@@" ]; then
+  NEED_LANDRUN=true
+fi
+#
+if [ "$NEED_DOWNLOAD" = "false" ] && [ "$NEED_LANDRUN" = "false" ]; then
+  echo "OLLIE_LOADER_START {\"need_download\":false,\"need_landrun\":false}" >&2
 else
   # Find base64 decoder
   if command -v base64 >/dev/null 2>&1; then
@@ -32,24 +44,41 @@ else
   command -v gunzip >/dev/null 2>&1 || GUNZIP_CMD="gzip -d"
   #
   mkdir -p "$CACHE_DIR"
-  echo "OLLIE_LOADER_START {\"need_download\":true}" >&2
+  echo "OLLIE_LOADER_START {\"need_download\":$NEED_DOWNLOAD,\"need_landrun\":$NEED_LANDRUN}" >&2
   #
-  # Read download size, then binary data
-  while IFS= read -r line; do
-    case "$line" in
-      OLLIE_DOWNLOAD\ *) BINARY_LENGTH="${line#OLLIE_DOWNLOAD }"; break ;;
-    esac
-  done
-  #
-  CACHE_TMP="$CACHE_BIN.tmp.$$"
-  if ! head -c "$BINARY_LENGTH" | $BASE64_CMD | $GUNZIP_CMD > "$CACHE_TMP"; then
-    rm -f "$CACHE_TMP"
-    echo "ERROR: binary transfer failed" >&2
-    exit 1
+  if [ "$NEED_DOWNLOAD" = "true" ]; then
+    while IFS= read -r line; do
+      case "$line" in
+        OLLIE_DOWNLOAD\ *) BINARY_LENGTH="${line#OLLIE_DOWNLOAD }"; break ;;
+      esac
+    done
+    CACHE_TMP="$CACHE_BIN.tmp.$$"
+    if ! head -c "$BINARY_LENGTH" | $BASE64_CMD | $GUNZIP_CMD > "$CACHE_TMP"; then
+      rm -f "$CACHE_TMP"
+      echo "ERROR: ollie-remote transfer failed" >&2
+      exit 1
+    fi
+    chmod +x "$CACHE_TMP"
+    mv "$CACHE_TMP" "$CACHE_BIN"
+    echo "@@HASH@@" > "$CACHE_HASH"
+  fi
+  #
+  if [ "$NEED_LANDRUN" = "true" ]; then
+    while IFS= read -r line; do
+      case "$line" in
+        OLLIE_DOWNLOAD\ *) BINARY_LENGTH="${line#OLLIE_DOWNLOAD }"; break ;;
+      esac
+    done
+    CACHE_TMP="$CACHE_LANDRUN.tmp.$$"
+    if ! head -c "$BINARY_LENGTH" | $BASE64_CMD | $GUNZIP_CMD > "$CACHE_TMP"; then
+      rm -f "$CACHE_TMP"
+      echo "ERROR: landrun transfer failed" >&2
+      exit 1
+    fi
+    chmod +x "$CACHE_TMP"
+    mv "$CACHE_TMP" "$CACHE_LANDRUN"
+    echo "@@LANDRUN_HASH@@" > "$CACHE_LANDRUN_HASH"
   fi
-  chmod +x "$CACHE_TMP"
-  mv "$CACHE_TMP" "$CACHE_BIN"
-  echo "@@HASH@@" > "$CACHE_HASH"
   echo "OLLIE_LOADER_READY" >&2
 fi
 #
diff --git a/toolsrv/remote.go b/toolsrv/remote.go
index cc98dee..6434dd2 100644
--- a/toolsrv/remote.go
+++ b/toolsrv/remote.go
@@ -77,9 +77,22 @@ func RemoteDial(ctx context.Context, cfg RemoteConfig) (*RemoteServer, error) {
 	hash := sha256.Sum256(binData)
 	hashStr := hex.EncodeToString(hash[:])
 
-	// Generate bootstrap script with hash and CWD baked in.
+	// Find landrun binary to deploy alongside ollie-remote.
+	landrunPath, err := exec.LookPath("landrun")
+	if err != nil {
+		return nil, fmt.Errorf("find landrun binary: %w", err)
+	}
+	landrunData, err := os.ReadFile(landrunPath)
+	if err != nil {
+		return nil, fmt.Errorf("read landrun binary: %w", err)
+	}
+	landrunHash := sha256.Sum256(landrunData)
+	landrunHashStr := hex.EncodeToString(landrunHash[:])
+
+	// Generate bootstrap script with hashes and CWD baked in.
 	bootstrap := bootstrapTemplate
 	bootstrap = strings.ReplaceAll(bootstrap, "@@HASH@@", hashStr)
+	bootstrap = strings.ReplaceAll(bootstrap, "@@LANDRUN_HASH@@", landrunHashStr)
 	cwdEscaped := shellEscape(cfg.CWD)
 	extraArgs := ""
 	if cfg.ToolsPath != "" {
@@ -132,6 +145,7 @@ func RemoteDial(ctx context.Context, cfg RemoteConfig) (*RemoteServer, error) {
 	// Monitor stderr for bootstrap messages.
 	type loaderMsg struct {
 		NeedDownload bool `json:"need_download"`
+		NeedLandrun  bool `json:"need_landrun"`
 	}
 
 	stderrScanner := bufio.NewScanner(stderrPipe)
@@ -144,7 +158,7 @@ func RemoteDial(ctx context.Context, cfg RemoteConfig) (*RemoteServer, error) {
 				var msg loaderMsg
 				json.Unmarshal([]byte(after), &msg)
 				loaderCh <- msg
-				if !msg.NeedDownload {
+				if !msg.NeedDownload && !msg.NeedLandrun {
 					close(readyCh)
 				}
 			} else if line == "OLLIE_LOADER_READY" {
@@ -159,8 +173,16 @@ func RemoteDial(ctx context.Context, cfg RemoteConfig) (*RemoteServer, error) {
 		if msg.NeedDownload {
 			if err := transferBinary(stdin, binData); err != nil {
 				cmd.Process.Kill()
-				return nil, fmt.Errorf("transfer binary: %w", err)
+				return nil, fmt.Errorf("transfer ollie-remote: %w", err)
 			}
+		}
+		if msg.NeedLandrun {
+			if err := transferBinary(stdin, landrunData); err != nil {
+				cmd.Process.Kill()
+				return nil, fmt.Errorf("transfer landrun: %w", err)
+			}
+		}
+		if msg.NeedDownload || msg.NeedLandrun {
 			// Wait for ready signal.
 			select {
 			case <-readyCh: