diff --git a/packages/cli/e2e/__tests__/fixtures/test-project/src/services/api/api.check.ts b/packages/cli/e2e/__tests__/fixtures/test-project/src/services/api/api.check.ts
index a348ed45e..dc938fafe 100644
--- a/packages/cli/e2e/__tests__/fixtures/test-project/src/services/api/api.check.ts
+++ b/packages/cli/e2e/__tests__/fixtures/test-project/src/services/api/api.check.ts
@@ -24,6 +24,7 @@ const apiCheck = new ApiCheck('homepage-api-check-1', {
 
 const skipSslApiCheck = new ApiCheck('ssl-api-check-1', {
   name: 'Skip SSL Check',
+  activated: false,
   alertChannels: [slackChannel, webhookChannel],
   degradedResponseTime: 10000,
   maxResponseTime: 20000,
diff --git a/packages/cli/e2e/__tests__/test.spec.ts b/packages/cli/e2e/__tests__/test.spec.ts
index b4c0f5db7..9be0e069a 100644
--- a/packages/cli/e2e/__tests__/test.spec.ts
+++ b/packages/cli/e2e/__tests__/test.spec.ts
@@ -51,7 +51,13 @@ describe('test', { timeout: 45000 }, () => {
 
     it('Test project should run successfully', async () => {
       const secretEnv = uuid.v4()
-      const result = await runTest(fixt, ['-e', `SECRET_ENV=${secretEnv}`, '--verbose'])
+      const result = await runTest(fixt, [
+        '-e',
+        `SECRET_ENV=${secretEnv}`,
+        '--verbose',
+        '--grep',
+        '^(?!Skip SSL Check$).*',
+      ])
       expect(result.stdout).not.toContain('File extension type example')
       expect(result.stdout).toContain(secretEnv)
     }, 130_000)
@@ -98,7 +104,9 @@ describe('test', { timeout: 45000 }, () => {
       } catch {
         // No-op
       }
-      const result = await runTest(fixt, ['--record', '--reporter', 'github'], {
+      // Keep this reporter test scoped to one stable check. The GitHub assertions below do not
+      // need the whole fixture project, and unrelated remote checks can make this fail first.
+      const result = await runTest(fixt, ['secret.check.ts', '--record', '--reporter', 'github'], {
         env: {
           CHECKLY_REPORTER_GITHUB_OUTPUT: reportFilename,
         },
diff --git a/packages/cli/src/constructs/__tests__/api-check.spec.ts b/packages/cli/src/constructs/__tests__/api-check.spec.ts
index 145eab535..b3588af34 100644
--- a/packages/cli/src/constructs/__tests__/api-check.spec.ts
+++ b/packages/cli/src/constructs/__tests__/api-check.spec.ts
@@ -272,6 +272,34 @@ describe('ApiCheck', () => {
     }))
   }, DEFAULT_TEST_TIMEOUT)
 
+  it('should synthesize skipSSL requests', async () => {
+    const output = await parseProject(
+      fixt,
+      '--config',
+      fixt.abspath('test-cases/test-skip-ssl/checkly.config.js'),
+    )
+
+    expect(output).toEqual(expect.objectContaining({
+      diagnostics: expect.objectContaining({
+        fatal: false,
+      }),
+      payload: expect.objectContaining({
+        resources: expect.arrayContaining([
+          expect.objectContaining({
+            logicalId: 'check',
+            type: 'check',
+            member: true,
+            payload: expect.objectContaining({
+              request: expect.objectContaining({
+                skipSSL: true,
+              }),
+            }),
+          }),
+        ]),
+      }),
+    }))
+  }, DEFAULT_TEST_TIMEOUT)
+
   describe('retryStrategy', () => {
     it('should synthesize `onlyOn`', async () => {
       const output = await parseProject(
diff --git a/packages/cli/src/constructs/__tests__/fixtures/api-check/test-cases/test-skip-ssl/checkly.config.js b/packages/cli/src/constructs/__tests__/fixtures/api-check/test-cases/test-skip-ssl/checkly.config.js
new file mode 100644
index 000000000..19a81a24e
--- /dev/null
+++ b/packages/cli/src/constructs/__tests__/fixtures/api-check/test-cases/test-skip-ssl/checkly.config.js
@@ -0,0 +1,11 @@
+import { defineConfig } from 'checkly'
+
+const config = defineConfig({
+  projectName: 'Check Fixture',
+  logicalId: 'check-fixture',
+  checks: {
+    checkMatch: '**/*.check.js',
+  },
+})
+
+export default config
diff --git a/packages/cli/src/constructs/__tests__/fixtures/api-check/test-cases/test-skip-ssl/test.check.js b/packages/cli/src/constructs/__tests__/fixtures/api-check/test-cases/test-skip-ssl/test.check.js
new file mode 100644
index 000000000..612b5d540
--- /dev/null
+++ b/packages/cli/src/constructs/__tests__/fixtures/api-check/test-cases/test-skip-ssl/test.check.js
@@ -0,0 +1,11 @@
+import { ApiCheck } from 'checkly/constructs'
+
+new ApiCheck('check', {
+  name: 'Skip SSL Check',
+  request: {
+    method: 'GET',
+    // This fixture is parsed and synthesized only; it must never perform a network request.
+    url: 'https://self-signed.example.test',
+    skipSSL: true,
+  },
+})