diff --git a/src/runtime/LocalRuntime.ts b/src/runtime/LocalRuntime.ts
index 4b01216e8..95818b758 100644
--- a/src/runtime/LocalRuntime.ts
+++ b/src/runtime/LocalRuntime.ts
@@ -303,6 +303,16 @@ export class LocalRuntime implements Runtime {
     }
   }
 
+  normalizePath(targetPath: string, basePath: string): string {
+    // For local runtime, use Node.js path resolution
+    // Handle special case: current directory
+    const target = targetPath.trim();
+    if (target === ".") {
+      return path.resolve(basePath);
+    }
+    return path.resolve(basePath, target);
+  }
+
   getWorkspacePath(projectPath: string, workspaceName: string): string {
     const projectName = getProjectName(projectPath);
     return path.join(this.srcBaseDir, projectName, workspaceName);
diff --git a/src/runtime/Runtime.ts b/src/runtime/Runtime.ts
index 0bfd1af25..28f8fd9b4 100644
--- a/src/runtime/Runtime.ts
+++ b/src/runtime/Runtime.ts
@@ -195,6 +195,25 @@ export interface Runtime {
    */
   stat(path: string): Promise<FileStat>;
 
+  /**
+   * Normalize a path for comparison purposes within this runtime's context.
+   * Handles runtime-specific path semantics (local vs remote).
+   *
+   * @param targetPath Path to normalize (may be relative or absolute)
+   * @param basePath Base path to resolve relative paths against
+   * @returns Normalized path suitable for string comparison
+   *
+   * @example
+   * // LocalRuntime
+   * runtime.normalizePath(".", "/home/user") // => "/home/user"
+   * runtime.normalizePath("../other", "/home/user/project") // => "/home/user/other"
+   *
+   * // SSHRuntime
+   * runtime.normalizePath(".", "/home/user") // => "/home/user"
+   * runtime.normalizePath("~/project", "~") // => "~/project"
+   */
+  normalizePath(targetPath: string, basePath: string): string;
+
   /**
    * Compute absolute workspace path from project and workspace name.
    * This is the SINGLE source of truth for workspace path computation.
diff --git a/src/runtime/SSHRuntime.ts b/src/runtime/SSHRuntime.ts
index 7c19f3d27..4b86d916b 100644
--- a/src/runtime/SSHRuntime.ts
+++ b/src/runtime/SSHRuntime.ts
@@ -317,6 +317,41 @@ export class SSHRuntime implements Runtime {
     };
   }
 
+  normalizePath(targetPath: string, basePath: string): string {
+    // For SSH, handle paths in a POSIX-like manner without accessing the remote filesystem
+    const target = targetPath.trim();
+    let base = basePath.trim();
+
+    // Normalize base path - remove trailing slash (except for root "/")
+    if (base.length > 1 && base.endsWith("/")) {
+      base = base.slice(0, -1);
+    }
+
+    // Handle special case: current directory
+    if (target === ".") {
+      return base;
+    }
+
+    // Handle tilde expansion - keep as-is for comparison
+    let normalizedTarget = target;
+    if (target === "~" || target.startsWith("~/")) {
+      normalizedTarget = target;
+    } else if (target.startsWith("/")) {
+      // Absolute path - use as-is
+      normalizedTarget = target;
+    } else {
+      // Relative path - resolve against base using POSIX path joining
+      normalizedTarget = base.endsWith("/") ? base + target : base + "/" + target;
+    }
+
+    // Remove trailing slash for comparison (except for root "/")
+    if (normalizedTarget.length > 1 && normalizedTarget.endsWith("/")) {
+      normalizedTarget = normalizedTarget.slice(0, -1);
+    }
+
+    return normalizedTarget;
+  }
+
   /**
    * Build common SSH arguments based on runtime config
    * @param includeHost - Whether to include the host in the args (for direct ssh commands)
diff --git a/src/services/tools/bash.test.ts b/src/services/tools/bash.test.ts
index fc58458e6..0542280b2 100644
--- a/src/services/tools/bash.test.ts
+++ b/src/services/tools/bash.test.ts
@@ -1235,3 +1235,138 @@ fi
     expect(remainingProcesses).toBe(0);
   });
 });
+
+describe("SSH runtime redundant cd detection", () => {
+  // Helper to create bash tool with SSH runtime configuration
+  // Note: These tests check redundant cd detection logic only - they don't actually execute via SSH
+  function createTestBashToolWithSSH(cwd: string) {
+    const tempDir = new TestTempDir("test-bash-ssh");
+    const sshRuntime = createRuntime({
+      type: "ssh",
+      host: "test-host",
+      srcBaseDir: "/remote/base",
+    });
+
+    const tool = createBashTool({
+      cwd,
+      runtime: sshRuntime,
+      tempDir: tempDir.path,
+    });
+
+    return {
+      tool,
+      [Symbol.dispose]() {
+        tempDir[Symbol.dispose]();
+      },
+    };
+  }
+
+  it("should reject redundant cd to absolute path on SSH runtime", async () => {
+    const remoteCwd = "/home/user/project";
+    using testEnv = createTestBashToolWithSSH(remoteCwd);
+    const tool = testEnv.tool;
+
+    const args: BashToolArgs = {
+      script: `cd ${remoteCwd} && echo test`,
+      timeout_secs: 5,
+    };
+
+    const result = (await tool.execute!(args, mockToolCallOptions)) as BashToolResult;
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain("Redundant cd");
+      expect(result.error).toContain("already runs in");
+    }
+  });
+
+  it("should reject redundant cd with relative path (.) on SSH runtime", async () => {
+    const remoteCwd = "/home/user/project";
+    using testEnv = createTestBashToolWithSSH(remoteCwd);
+    const tool = testEnv.tool;
+
+    const args: BashToolArgs = {
+      script: "cd . && echo test",
+      timeout_secs: 5,
+    };
+
+    const result = (await tool.execute!(args, mockToolCallOptions)) as BashToolResult;
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain("Redundant cd");
+    }
+  });
+
+  it("should reject redundant cd with tilde path on SSH runtime", async () => {
+    const remoteCwd = "~/project";
+    using testEnv = createTestBashToolWithSSH(remoteCwd);
+    const tool = testEnv.tool;
+
+    const args: BashToolArgs = {
+      script: "cd ~/project && echo test",
+      timeout_secs: 5,
+    };
+
+    const result = (await tool.execute!(args, mockToolCallOptions)) as BashToolResult;
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain("Redundant cd");
+    }
+  });
+
+  it("should reject redundant cd with single tilde on SSH runtime", async () => {
+    const remoteCwd = "~";
+    using testEnv = createTestBashToolWithSSH(remoteCwd);
+    const tool = testEnv.tool;
+
+    const args: BashToolArgs = {
+      script: "cd ~ && echo test",
+      timeout_secs: 5,
+    };
+
+    const result = (await tool.execute!(args, mockToolCallOptions)) as BashToolResult;
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain("Redundant cd");
+    }
+  });
+
+  it("should handle trailing slashes in path comparison on SSH runtime", async () => {
+    const remoteCwd = "/home/user/project";
+    using testEnv = createTestBashToolWithSSH(remoteCwd);
+    const tool = testEnv.tool;
+
+    const args: BashToolArgs = {
+      script: "cd /home/user/project/ && echo test",
+      timeout_secs: 5,
+    };
+
+    const result = (await tool.execute!(args, mockToolCallOptions)) as BashToolResult;
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain("Redundant cd");
+    }
+  });
+
+  it("should handle cwd with trailing slash on SSH runtime", async () => {
+    const remoteCwd = "/home/user/project/";
+    using testEnv = createTestBashToolWithSSH(remoteCwd);
+    const tool = testEnv.tool;
+
+    const args: BashToolArgs = {
+      script: "cd /home/user/project && echo test",
+      timeout_secs: 5,
+    };
+
+    const result = (await tool.execute!(args, mockToolCallOptions)) as BashToolResult;
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain("Redundant cd");
+    }
+  });
+});
diff --git a/src/services/tools/bash.ts b/src/services/tools/bash.ts
index 23dbcabfa..8def72db6 100644
--- a/src/services/tools/bash.ts
+++ b/src/services/tools/bash.ts
@@ -77,17 +77,15 @@ export const createBashTool: ToolFactory = (config: ToolConfiguration) => {
       let fileTruncated = false; // Hit 100KB file limit
 
       // Detect redundant cd to working directory
-      // Note: config.cwd is the actual execution path (local for LocalRuntime, remote for SSHRuntime)
-      // Match patterns like: "cd /path &&", "cd /path;", "cd '/path' &&", "cd "/path" &&"
+      // Delegate path normalization to the runtime for proper handling of local vs remote paths
       const cdPattern = /^\s*cd\s+['"]?([^'";\\&|]+)['"]?\s*[;&|]/;
       const match = cdPattern.exec(script);
       if (match) {
         const targetPath = match[1].trim();
-        // For SSH runtime, config.cwd might use $HOME - need to handle this
-        // Normalize paths for comparison (resolve to absolute where possible)
-        // Note: This check is best-effort - it won't catch all cases on SSH (e.g., ~/path vs $HOME/path)
-        const normalizedTarget = path.resolve(config.cwd, targetPath);
-        const normalizedCwd = path.resolve(config.cwd);
+
+        // Use runtime's normalizePath method to handle path comparison correctly
+        const normalizedTarget = config.runtime.normalizePath(targetPath, config.cwd);
+        const normalizedCwd = config.runtime.normalizePath(".", config.cwd);
 
         if (normalizedTarget === normalizedCwd) {
           return {