diff --git a/test/jest/acceptance/proxy-behavior.spec.ts b/test/jest/acceptance/proxy-behavior.spec.ts
new file mode 100644
index 0000000000..972c8a6dc8
--- /dev/null
+++ b/test/jest/acceptance/proxy-behavior.spec.ts
@@ -0,0 +1,119 @@
+import { exec } from 'child_process';
+import { sep } from 'path';
+const main = './dist/cli/index.js'.replace(/\//g, sep);
+
+const SNYK_API_HTTPS = 'https://snyk.io/api/v1';
+const SNYK_API_HTTP = 'http://snyk.io/api/v1';
+const FAKE_HTTP_PROXY = 'http://localhost:12345';
+const testTimeout = 50000;
+
+describe('Proxy configuration behavior', () => {
+  describe('*_PROXY against HTTPS host', () => {
+    it(
+      'tries to connect to the HTTPS_PROXY when HTTPS_PROXY is set',
+      (done) => {
+        exec(
+          `node ${main} woof -d`,
+          {
+            env: {
+              HTTPS_PROXY: FAKE_HTTP_PROXY,
+              SNYK_API: SNYK_API_HTTPS,
+            },
+          },
+          (err, stdout, stderr) => {
+            if (err) {
+              throw err;
+            }
+
+            expect(stderr).toContain(
+              `snyk analytics Error: connect ECONNREFUSED 127.0.0.1:${
+                FAKE_HTTP_PROXY.split(':')[2]
+              }`,
+            );
+            done();
+          },
+        );
+      },
+      testTimeout,
+    );
+
+    it(
+      'does not try to connect to the HTTP_PROXY when it is set',
+      (done) => {
+        exec(
+          `node ${main} woof -d`,
+          {
+            env: {
+              HTTP_PROXY: FAKE_HTTP_PROXY,
+              SNYK_API: SNYK_API_HTTPS,
+            },
+          },
+          (err, stdout, stderr) => {
+            if (err) {
+              throw err;
+            }
+
+            expect(stderr).not.toContain('ECONNREFUSED');
+            done();
+          },
+        );
+      },
+      testTimeout,
+    );
+  });
+
+  describe('*_PROXY against HTTP host', () => {
+    it(
+      'tries to connect to the HTTP_PROXY when HTTP_PROXY is set',
+      (done) => {
+        exec(
+          `node ${main} woof -d`,
+          {
+            env: {
+              HTTP_PROXY: FAKE_HTTP_PROXY,
+              SNYK_API: SNYK_API_HTTP,
+              SNYK_HTTP_PROTOCOL_UPGRADE: '0',
+            },
+          },
+          (err, stdout, stderr) => {
+            if (err) {
+              throw err;
+            }
+
+            expect(stderr).toContain(
+              `snyk analytics Error: connect ECONNREFUSED 127.0.0.1:${
+                FAKE_HTTP_PROXY.split(':')[2]
+              }`,
+            );
+            done();
+          },
+        );
+      },
+      testTimeout,
+    );
+
+    it(
+      'does not try to connect to the HTTPS_PROXY when it is set',
+      (done) => {
+        exec(
+          `node ${main} woof -d`,
+          {
+            env: {
+              HTTPS_PROXY: FAKE_HTTP_PROXY,
+              SNYK_API: SNYK_API_HTTP,
+              SNYK_HTTP_PROTOCOL_UPGRADE: '0',
+            },
+          },
+          (err, stdout, stderr) => {
+            // TODO: incorrect behavior when Needle tries to upgrade connection after 301 http->https and the Agent option is set to a strict protocol
+            expect(stderr).toContain(
+              'TypeError [ERR_INVALID_PROTOCOL]: Protocol "https:" not supported. Expected "http:"',
+            );
+            done();
+          },
+        );
+      },
+      testTimeout,
+    );
+  });
+});