diff --git a/src/client.ts b/src/client.ts
index a2b5e79..d5d8cc6 100644
--- a/src/client.ts
+++ b/src/client.ts
@@ -10,35 +10,10 @@ import type {
   InitializeParams,
   PublishDiagnosticsParams,
 } from "vscode-languageserver-protocol";
-import * as path from "node:path";
 import type { ServerConfig } from "./types.ts";
 import { ServerNotFoundError } from "./types.ts";
 import { findRoot, pathToUri, uriToPath } from "./root.ts";
-
-// Is On PATH - Returns true if `cmd` resolves to an executable via the
-// supplied PATH. Absolute/relative paths are checked directly.
-function isOnPath(cmd: string, env: NodeJS.ProcessEnv): boolean {
-  const isExec = (p: string) => {
-    try {
-      fs.accessSync(p, fs.constants.X_OK);
-      return true;
-    } catch {
-      return false;
-    }
-  };
-  if (cmd.includes(path.sep)) return isExec(cmd);
-  const exts =
-    process.platform === "win32"
-      ? (env.PATHEXT ?? ".EXE;.CMD;.BAT").split(";")
-      : [""];
-  for (const dir of (env.PATH ?? "").split(path.delimiter)) {
-    if (!dir) continue;
-    for (const ext of exts) {
-      if (isExec(path.join(dir, cmd + ext))) return true;
-    }
-  }
-  return false;
-}
+import { isOnPath } from "./util.ts";
 
 // LspClient - Thin wrapper that spawns a language server, performs the
 // initialize handshake, auto-opens a file, and exposes sendRequest so the
diff --git a/src/root.ts b/src/root.ts
index 3cdb3d3..ae5eb74 100644
--- a/src/root.ts
+++ b/src/root.ts
@@ -4,6 +4,7 @@ import { pathToFileURL, fileURLToPath } from "node:url";
 import { servers, globalRootMarkers } from "../server.ts";
 import type { ServerConfig } from "./types.ts";
 import { UnsupportedExtensionError } from "./types.ts";
+import { isOnPath } from "./util.ts";
 
 // Resolve File URI To Local Path
 export function uriToPath(uri: string): string {
@@ -15,11 +16,24 @@ export function pathToUri(p: string): string {
   return pathToFileURL(path.resolve(p)).toString();
 }
 
+// Server Availability Cache - Checked once per process lifetime per server.
+// Avoids repeated filesystem lookups on every tool call.
+const serverAvailability = new Map<string, boolean>();
+
+// Is Server Available - Returns true if the server binary is on PATH.
+// Result is cached for the lifetime of this process.
+export function isServerAvailable(server: ServerConfig): boolean {
+  if (serverAvailability.has(server.id)) return serverAvailability.get(server.id)!;
+  const available = isOnPath(server.command, process.env);
+  serverAvailability.set(server.id, available);
+  return available;
+}
+
 // Pick Server By File Extension - match[] entries are matched against the
-// file's extension (no dot). First server in the registry wins.
+// file's extension (no dot). First available server in the registry wins.
 export function pickServer(filePath: string): ServerConfig {
   const ext = path.extname(filePath).replace(/^\./, "");
-  const hit = servers.find((s) => s.match.includes(ext));
+  const hit = servers.find((s) => s.match.includes(ext) && isServerAvailable(s));
   if (!hit) {
     throw new UnsupportedExtensionError(`.${ext}`);
   }
diff --git a/src/util.ts b/src/util.ts
new file mode 100644
index 0000000..300bb37
--- /dev/null
+++ b/src/util.ts
@@ -0,0 +1,27 @@
+import * as fs from "node:fs";
+import * as path from "node:path";
+
+// Is On PATH - Returns true if `cmd` resolves to an executable via the
+// supplied PATH. Absolute/relative paths are checked directly.
+export function isOnPath(cmd: string, env: NodeJS.ProcessEnv): boolean {
+  const isExec = (p: string) => {
+    try {
+      fs.accessSync(p, fs.constants.X_OK);
+      return true;
+    } catch {
+      return false;
+    }
+  };
+  if (cmd.includes(path.sep)) return isExec(cmd);
+  const exts =
+    process.platform === "win32"
+      ? (env.PATHEXT ?? ".EXE;.CMD;.BAT").split(";")
+      : [""];
+  for (const dir of (env.PATH ?? "").split(path.delimiter)) {
+    if (!dir) continue;
+    for (const ext of exts) {
+      if (isExec(path.join(dir, cmd + ext))) return true;
+    }
+  }
+  return false;
+}