diff --git a/packages/core/src/evaluation/providers/cli.ts b/packages/core/src/evaluation/providers/cli.ts
index 2a98a85c..49701b2e 100644
--- a/packages/core/src/evaluation/providers/cli.ts
+++ b/packages/core/src/evaluation/providers/cli.ts
@@ -352,9 +352,15 @@ export class CliProvider implements Provider {
     );
     const renderedCommand = renderTemplate(this.config.command, templateValues);
 
+    // Use per-request cwd override (from workspace) if any request provides one,
+    // otherwise fall back to the target's configured cwd.
+    // All requests in a batch share the same workspace, so the first request's cwd
+    // is representative of the entire batch.
+    const effectiveCwd = requests[0]?.cwd ?? this.config.cwd;
+
     if (this.verbose) {
       console.log(
-        `[cli-provider:${this.targetName}] (batch size=${requests.length}) cwd=${this.config.cwd ?? ''} command=${renderedCommand}`,
+        `[cli-provider:${this.targetName}] (batch size=${requests.length}) cwd=${effectiveCwd ?? ''} command=${renderedCommand}`,
       );
     }
 
@@ -362,7 +368,7 @@ export class CliProvider implements Provider {
     try {
       const startTime = Date.now();
       const result = await this.runCommand(renderedCommand, {
-        cwd: this.config.cwd,
+        cwd: effectiveCwd,
         env: process.env,
         timeoutMs: this.config.timeoutMs,
         signal: controller.signal,
@@ -402,7 +408,7 @@ export class CliProvider implements Provider {
               command: renderedCommand,
               stderr: result.stderr,
               exitCode: result.exitCode ?? 0,
-              cwd: this.config.cwd,
+              cwd: effectiveCwd,
               outputFile: outputFilePath,
             },
           };
@@ -423,7 +429,7 @@ export class CliProvider implements Provider {
               command: renderedCommand,
               stderr: result.stderr,
               exitCode: result.exitCode ?? 0,
-              cwd: this.config.cwd,
+              cwd: effectiveCwd,
               outputFile: outputFilePath,
               error: errorMessage,
             },
@@ -439,7 +445,7 @@ export class CliProvider implements Provider {
             command: renderedCommand,
             stderr: result.stderr,
             exitCode: result.exitCode ?? 0,
-            cwd: this.config.cwd,
+            cwd: effectiveCwd,
             outputFile: outputFilePath,
             recordId: evalCaseId,
           },
diff --git a/packages/core/test/evaluation/orchestrator.test.ts b/packages/core/test/evaluation/orchestrator.test.ts
index 4249b9fe..a5134076 100644
--- a/packages/core/test/evaluation/orchestrator.test.ts
+++ b/packages/core/test/evaluation/orchestrator.test.ts
@@ -223,6 +223,38 @@ describe('runTestCase', () => {
     expect(provider.callIndex).toBe(1);
   });
 
+  it('preserves workspace cwd across retry attempts', async () => {
+    const cwdsSeen: (string | undefined)[] = [];
+    const provider: Provider = {
+      id: 'mock:cwd-test',
+      kind: 'mock' as const,
+      targetName: 'cwd-test',
+      async invoke(request: ProviderRequest): Promise<ProviderResponse> {
+        cwdsSeen.push(request.cwd);
+        if (cwdsSeen.length === 1) {
+          throw new Error('Transient failure');
+        }
+        return {
+          output: [{ role: 'assistant', content: 'Success on retry' }],
+        };
+      },
+    };
+
+    const result = await runEvalCase({
+      evalCase: baseTestCase,
+      provider,
+      target: baseTarget,
+      evaluators: evaluatorRegistry,
+      maxRetries: 1,
+      sharedWorkspacePath: '/fake/workspace/path',
+    });
+
+    expect(result.score).toBeGreaterThan(0);
+    expect(cwdsSeen).toHaveLength(2);
+    expect(cwdsSeen[0]).toBe('/fake/workspace/path');
+    expect(cwdsSeen[1]).toBe('/fake/workspace/path');
+  });
+
   it('retries provider errors up to maxRetries', async () => {
     const provider = new SequenceProvider('mock', {
       errors: [new Error('Request timeout')],
diff --git a/packages/core/test/evaluation/providers/cli.test.ts b/packages/core/test/evaluation/providers/cli.test.ts
index ec08d427..0d2958a8 100644
--- a/packages/core/test/evaluation/providers/cli.test.ts
+++ b/packages/core/test/evaluation/providers/cli.test.ts
@@ -138,6 +138,91 @@ describe('CliProvider', () => {
     await expect(provider.invoke(baseRequest)).rejects.toThrow(/timed out/i);
   });
 
+  it('uses request.cwd as working directory override in invoke', async () => {
+    let capturedCwd: string | undefined;
+    const runner = mock(async (command: string, options): Promise<CommandRunResult> => {
+      capturedCwd = options?.cwd;
+      const match = command.match(/agentv-case-1-\d+-\w+\.json/);
+      if (match) {
+        const outputFilePath = path.join(os.tmpdir(), match[0]);
+        await writeFile(outputFilePath, 'response', 'utf-8');
+        createdFiles.push(outputFilePath);
+      }
+      return { stdout: '', stderr: '', exitCode: 0, failed: false };
+    });
+
+    const configWithCwd: CliResolvedConfig = { ...baseConfig, cwd: '/config/cwd' };
+    const provider = new CliProvider('cli-target', configWithCwd, runner);
+
+    // request.cwd should override config.cwd
+    await provider.invoke({ ...baseRequest, cwd: '/workspace/path' });
+    expect(capturedCwd).toBe('/workspace/path');
+  });
+
+  it('falls back to config.cwd when request.cwd is undefined in invoke', async () => {
+    let capturedCwd: string | undefined;
+    const runner = mock(async (command: string, options): Promise<CommandRunResult> => {
+      capturedCwd = options?.cwd;
+      const match = command.match(/agentv-case-1-\d+-\w+\.json/);
+      if (match) {
+        const outputFilePath = path.join(os.tmpdir(), match[0]);
+        await writeFile(outputFilePath, 'response', 'utf-8');
+        createdFiles.push(outputFilePath);
+      }
+      return { stdout: '', stderr: '', exitCode: 0, failed: false };
+    });
+
+    const configWithCwd: CliResolvedConfig = { ...baseConfig, cwd: '/config/cwd' };
+    const provider = new CliProvider('cli-target', configWithCwd, runner);
+
+    await provider.invoke(baseRequest); // no cwd in request
+    expect(capturedCwd).toBe('/config/cwd');
+  });
+
+  it('uses request.cwd as working directory override in invokeBatch', async () => {
+    let capturedCwd: string | undefined;
+    const runner = mock(async (command: string, options): Promise<CommandRunResult> => {
+      capturedCwd = options?.cwd;
+      const match = command.match(/agentv-batch-\d+-\w+\.jsonl/);
+      if (match) {
+        const outputFilePath = path.join(os.tmpdir(), match[0]);
+        const jsonl = `${JSON.stringify({ id: 'case-1', text: 'ok' })}\n`;
+        await writeFile(outputFilePath, jsonl, 'utf-8');
+        createdFiles.push(outputFilePath);
+      }
+      return { stdout: '', stderr: '', exitCode: 0, failed: false };
+    });
+
+    const configWithCwd: CliResolvedConfig = { ...baseConfig, cwd: '/config/cwd' };
+    const provider = new CliProvider('cli-target', configWithCwd, runner);
+
+    // First request's cwd should override config.cwd for the batch
+    await provider.invokeBatch([{ ...baseRequest, cwd: '/workspace/path' }]);
+    expect(capturedCwd).toBe('/workspace/path');
+  });
+
+  it('falls back to config.cwd when request.cwd is undefined in invokeBatch', async () => {
+    let capturedCwd: string | undefined;
+    const runner = mock(async (command: string, options): Promise<CommandRunResult> => {
+      capturedCwd = options?.cwd;
+      const match = command.match(/agentv-batch-\d+-\w+\.jsonl/);
+      if (match) {
+        const outputFilePath = path.join(os.tmpdir(), match[0]);
+        const jsonl = `${JSON.stringify({ id: 'case-1', text: 'ok' })}\n`;
+        await writeFile(outputFilePath, jsonl, 'utf-8');
+        createdFiles.push(outputFilePath);
+      }
+      return { stdout: '', stderr: '', exitCode: 0, failed: false };
+    });
+
+    const configWithCwd: CliResolvedConfig = { ...baseConfig, cwd: '/config/cwd' };
+    const provider = new CliProvider('cli-target', configWithCwd, runner);
+
+    // No cwd in request — should fall back to config.cwd
+    await provider.invokeBatch([baseRequest]);
+    expect(capturedCwd).toBe('/config/cwd');
+  });
+
   it('supports batch mode by reading JSONL records keyed by id', async () => {
     const runner = mock(async (command: string): Promise<CommandRunResult> => {
       const match = command.match(/agentv-batch-\d+-\w+\.jsonl/);