diff --git a/cli/CHANGELOG.md b/cli/CHANGELOG.md
index f673523705..d666b4417c 100644
--- a/cli/CHANGELOG.md
+++ b/cli/CHANGELOG.md
@@ -6,6 +6,7 @@ _Released 7/15/2025 (PENDING)_
 **Bugfixes:**
 
 - Fixed a regression introduced in [`14.5.0`](https://docs.cypress.io/guides/references/changelog#14-5-0) where the Stop button would not immediately stop the spec timer. Addresses [#31920](https://github.com/cypress-io/cypress/issues/31920).
+- Fixed an issue with the `CloudRequest` where it used the wrong port for `https` requests. Addressed in [#31992](https://github.com/cypress-io/cypress/pull/31992).
 
 ## 14.5.1
 
diff --git a/packages/network/lib/agent.ts b/packages/network/lib/agent.ts
index 4848a0a344..978a4b980e 100644
--- a/packages/network/lib/agent.ts
+++ b/packages/network/lib/agent.ts
@@ -126,7 +126,7 @@ export const createProxySock = (opts: CreateProxySockOpts, cb: CreateProxySockCb
 
 export const isRequestHttps = (options: http.RequestOptions) => {
   // WSS connections will not have an href, but you can tell protocol from the defaultAgent
-  return _.get(options, '_defaultAgent.protocol') === 'https:' || (options.href || '').slice(0, 6) === 'https:'
+  return _.get(options, '_defaultAgent.protocol') === 'https:' || options.protocol === 'https:' || (options.href || '').slice(0, 6) === 'https:'
 }
 
 export const isResponseStatusCode200 = (head: string) => {
@@ -226,6 +226,11 @@ export class CombinedAgent {
 
     const isHttps = isRequestHttps(options)
 
+    // Ensure that HTTPS requests are using 443
+    if (isHttps && options.port === 80) {
+      options.port = 443
+    }
+
     if (!options.href) {
       // options.path can contain query parameters, which url.format will not-so-kindly urlencode for us...
       // so just append it to the resultant URL string
diff --git a/packages/server/test/unit/cloud/api/cloud_request_spec.ts b/packages/server/test/unit/cloud/api/cloud_request_spec.ts
index 7f3f6db6ee..999db03af7 100644
--- a/packages/server/test/unit/cloud/api/cloud_request_spec.ts
+++ b/packages/server/test/unit/cloud/api/cloud_request_spec.ts
@@ -6,7 +6,7 @@ import agent from '@packages/network/lib/agent'
 import axios, { CreateAxiosDefaults, AxiosInstance } from 'axios'
 import debugLib from 'debug'
 import stripAnsi from 'strip-ansi'
-import { createCloudRequest } from '../../../../lib/cloud/api/cloud_request'
+import { CloudRequest, createCloudRequest } from '../../../../lib/cloud/api/cloud_request'
 import cloudApi from '../../../../lib/cloud/api'
 import app_config from '../../../../config/app.json'
 import os from 'os'
@@ -14,6 +14,9 @@ import pkg from '@packages/root'
 import { transformError } from '../../../../lib/cloud/api/axios_middleware/transform_error'
 import { DestroyableProxy, fakeServer, fakeProxy } from './utils/fake_proxy_server'
 import dedent from 'dedent'
+import { PassThrough } from 'stream'
+import fetch from 'cross-fetch'
+import nock from 'nock'
 
 chai.use(sinonChai)
 
@@ -444,6 +447,48 @@ describe('CloudRequest', () => {
     })
   })
 
+  describe('https requests', () => {
+    it('handles https requests properly', async () => {
+      nock.restore()
+
+      // @ts-ignore
+      const addRequestSpy = sinon.stub(agent.httpsAgent, 'addRequest').callsFake((req, options) => {
+        // fake IncomingMessage
+        const res = new PassThrough() as any
+
+        res.statusCode = 200
+        res.headers = {
+          'content-type': 'application/json',
+        }
+
+        process.nextTick(() => {
+          req.emit('response', res)
+          res.write(JSON.stringify({ ok: options.port === 443 && options.protocol === 'https:' }))
+          res.end()
+        })
+      })
+
+      const result1 = await CloudRequest.post('https://cloud.cypress.io/ping', {})
+
+      expect(result1.data).to.eql({ ok: true })
+
+      const result2 = await createCloudRequest({ baseURL: 'https://api.cypress.io' }).post('/ping', {})
+
+      expect(result2.data).to.eql({ ok: true })
+
+      const result3 = await fetch('https://cloud.cypress.io/ping', {
+        method: 'POST',
+        body: '{}',
+        // @ts-expect-error - this is supported
+        agent,
+      })
+
+      expect(await result3.json()).to.eql({ ok: true })
+
+      expect(addRequestSpy).to.have.been.calledThrice
+    })
+  })
+
   ;[undefined, 'development', 'test', 'staging', 'production'].forEach((env) => {
     describe(`base url for CYPRESS_CONFIG_ENV "${env}"`, () => {
       let prevEnv