diff --git a/.circleci/config.yml b/.circleci/config.yml
index f97a8f9e7a..55370e21f5 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -931,6 +931,35 @@ workflows:
           pre_test_cmds: |
             if (Test-Path '<< pipeline.parameters.windows_cache_dir >>/<< pipeline.parameters.windows_env_script >>') { . '<< pipeline.parameters.windows_cache_dir >>/<< pipeline.parameters.windows_env_script >>' }
 
+      - acceptance-tests:
+          name: acceptance-tests windows unmanaged pre-prod
+          go_target_os: windows
+          go_os: windows
+          go_arch: amd64
+          go_download_base_url: << pipeline.parameters.go_download_base_url >>
+          context:
+            - nodejs-install
+            - team_hammerhead-cli
+          filters:
+            branches:
+              ignore:
+                - main
+                - '/release.*/'
+          requires:
+            - build windows amd64
+          executor: win-server2022-amd64
+          test_snyk_command: binary-releases\\snyk-win.exe
+          install_deps_extension: windows-native-build
+          dont_skip_tests: 0
+          shards: 1
+          shard_calc_cmd: '$([int]$env:CIRCLE_NODE_INDEX + 1)'
+          additional_test_args: --runTestsByPath test/jest/acceptance/snyk-test/unmanaged-pre-prod.spec.ts
+          pre_test_cmds: |
+            if (Test-Path '<< pipeline.parameters.windows_cache_dir >>/<< pipeline.parameters.windows_env_script >>') { . '<< pipeline.parameters.windows_cache_dir >>/<< pipeline.parameters.windows_env_script >>' }
+            $env:TEST_SNYK_API = $env:TEST_SNYK_API_DEV
+            $env:TEST_SNYK_TOKEN = $env:TEST_SNYK_TOKEN_DEV
+            $env:TEST_SNYK_TOKEN_2 = $env:TEST_SNYK_TOKEN_DEV
+
       - sign:
           name: sign windows amd64
           context: snyk-windows-signing
@@ -1559,6 +1588,9 @@ jobs:
       pre_test_cmds:
         type: string
         default: 'echo Running tests'
+      additional_test_args:
+        type: string
+        default: ''
       shards:
         type: integer
         default: 4
@@ -1593,7 +1625,7 @@ jobs:
           no_output_timeout: 30m
           command: |
             << parameters.pre_test_cmds >>
-            npm run test:acceptance -- --selectProjects coreCli --shard=<< parameters.shard_calc_cmd >>/<< parameters.shards >>
+            npm run test:acceptance -- --selectProjects coreCli << parameters.additional_test_args >> --shard=<< parameters.shard_calc_cmd >>/<< parameters.shards >>
           environment:
             TEST_SNYK_FIPS: << parameters.fips >>
             TEST_SNYK_COMMAND: << parameters.test_snyk_command >>
diff --git a/test/jest/acceptance/snyk-test/unmanaged-pre-prod.spec.ts b/test/jest/acceptance/snyk-test/unmanaged-pre-prod.spec.ts
new file mode 100644
index 0000000000..24aa37da23
--- /dev/null
+++ b/test/jest/acceptance/snyk-test/unmanaged-pre-prod.spec.ts
@@ -0,0 +1,97 @@
+import { describeIf } from '../../../utils';
+import {
+  createProjectFromFixture,
+  createProjectFromWorkspace,
+} from '../../util/createProject';
+import { runSnykCLI } from '../../util/runSnykCLI';
+import * as path from 'path';
+
+jest.setTimeout(1000 * 60 * 5);
+
+const hasPreProdCredentials = Boolean(
+  process.env.TEST_SNYK_API_DEV && process.env.TEST_SNYK_TOKEN_DEV,
+);
+
+const env = {
+  ...process.env,
+  SNYK_API: process.env.TEST_SNYK_API_DEV,
+  SNYK_TOKEN: process.env.TEST_SNYK_TOKEN_DEV,
+};
+
+describeIf(hasPreProdCredentials)('unmanaged pre-prod user journey', () => {
+  test('runs `snyk test --unmanaged` against pre-prod', async () => {
+    const project = await createProjectFromWorkspace('unmanaged');
+    const { code, stdout, stderr } = await runSnykCLI('test --unmanaged -d', {
+      cwd: project.path(),
+      env,
+    });
+
+    if (code !== 1) {
+      console.debug(stderr);
+      console.debug('---------------------------');
+      console.debug(stdout);
+    }
+
+    expect(code).toEqual(1);
+    expect(stdout).toContain('madler/zlib@1.2.11');
+    expect(stdout).toContain(
+      'Tested 1 dependency for known issues, found 2 issues.',
+    );
+  });
+
+  test('runs `snyk test --unmanaged --json` against pre-prod', async () => {
+    const project = await createProjectFromWorkspace('unmanaged');
+    const { code, stdout, stderr } = await runSnykCLI(
+      'test --unmanaged -d --json',
+      {
+        cwd: project.path(),
+        env,
+      },
+    );
+
+    console.debug(stderr);
+    console.debug('---------------------------');
+    console.debug(stdout);
+
+    const parsed = JSON.parse(stdout);
+    expect(parsed).toEqual(expect.any(Array));
+    expect(parsed.length).toBeGreaterThanOrEqual(1);
+    expect(parsed[0].vulnerabilities.length).toBeGreaterThanOrEqual(1);
+    expect(stdout).toContain('"purl": "pkg:generic/zlib@');
+
+    // Verify file paths are present in the response to confirm the
+    // backend correctly handles OS-specific path separators (e.g. Windows backslashes).
+    expect(parsed[0].depsFilePaths).toBeDefined();
+    const filePaths = Object.values(parsed[0].depsFilePaths).flat() as string[];
+    expect(filePaths.length).toBeGreaterThanOrEqual(1);
+  });
+
+  test('runs `snyk sbom --unmanaged --max-depth=1` against pre-prod', async () => {
+    const project = await createProjectFromFixture(
+      path.join('unmanaged', 'extraction'),
+    );
+    const { code, stdout, stderr } = await runSnykCLI(
+      `sbom --unmanaged --max-depth=1 --format=cyclonedx1.4+json --org=${process.env.TEST_SNYK_ORG_SLUGNAME} --debug`,
+      {
+        cwd: project.path(),
+        env,
+      },
+    );
+
+    if (code !== 0) {
+      console.debug(stderr);
+      console.debug('---------------------------');
+      console.debug(stdout);
+    }
+
+    expect(code).toEqual(0);
+
+    let sbom;
+    expect(() => {
+      sbom = JSON.parse(stdout);
+    }).not.toThrow();
+
+    expect(sbom.metadata.component.name).toEqual('root-node');
+    expect(sbom.components.length).toBeGreaterThanOrEqual(1);
+  });
+});