diff --git a/src/rules/passthrough-handling.ts b/src/rules/passthrough-handling.ts
index a13bcb685..3fdd8be58 100644
--- a/src/rules/passthrough-handling.ts
+++ b/src/rules/passthrough-handling.ts
@@ -24,12 +24,13 @@ import {
 // issues so far as possible, by closely emulating a Firefox Client Hello:
 const NEW_CURVES_SUPPORTED = areFFDHECurvesSupported(process.versions.openssl);
 
+const SSL_OP_LEGACY_SERVER_CONNECT = 1 << 2;
 const SSL_OP_TLSEXT_PADDING = 1 << 4;
 const SSL_OP_NO_ENCRYPT_THEN_MAC = 1 << 19;
 
 // All settings are designed to exactly match Firefox v103, since that's a good baseline
 // that seems to be widely accepted and is easy to emulate from Node.js.
-export const UPSTREAM_TLS_OPTIONS: tls.SecureContextOptions = {
+export const getUpstreamTlsOptions = (strictChecks: boolean): tls.SecureContextOptions => ({
     ecdhCurve: [
         'X25519',
         'prime256v1', // N.B. Equivalent to secp256r1
@@ -74,12 +75,20 @@ export const UPSTREAM_TLS_OPTIONS: tls.SecureContextOptions = {
         'AES128-SHA',
         'AES256-SHA'
     ].join(':'),
-    secureOptions: SSL_OP_TLSEXT_PADDING | SSL_OP_NO_ENCRYPT_THEN_MAC,
+    secureOptions: strictChecks
+        ? SSL_OP_TLSEXT_PADDING | SSL_OP_NO_ENCRYPT_THEN_MAC
+        : SSL_OP_TLSEXT_PADDING | SSL_OP_NO_ENCRYPT_THEN_MAC | SSL_OP_LEGACY_SERVER_CONNECT,
     ...({
         // Valid, but not included in Node.js TLS module types:
         requestOSCP: true
-    } as any)
-};
+    } as any),
+
+    // Allow TLSv1, if !strict:
+    minVersion: strictChecks ? tls.DEFAULT_MIN_VERSION : 'TLSv1',
+
+    // Skip certificate validation entirely, if not strict:
+    rejectUnauthorized: strictChecks,
+});
 
 // --- Various helpers for deriving parts of request/response data given partial overrides: ---
 
diff --git a/src/rules/requests/request-handlers.ts b/src/rules/requests/request-handlers.ts
index 4160b8a0b..ec2e7367f 100644
--- a/src/rules/requests/request-handlers.ts
+++ b/src/rules/requests/request-handlers.ts
@@ -75,7 +75,7 @@ import {
     getH2HeadersAfterModification,
     OVERRIDABLE_REQUEST_PSEUDOHEADERS,
     buildOverriddenBody,
-    UPSTREAM_TLS_OPTIONS,
+    getUpstreamTlsOptions,
     shouldUseStrictHttps,
     getClientRelativeHostname,
     getDnsLookupFunction
@@ -746,10 +746,7 @@ export class PassThroughHandler extends PassThroughHandlerDefinition {
                 agent,
 
                 // TLS options:
-                ...UPSTREAM_TLS_OPTIONS,
-                // Allow TLSv1, if !strict
-                minVersion: strictHttpsChecks ? tls.DEFAULT_MIN_VERSION : 'TLSv1',
-                rejectUnauthorized: strictHttpsChecks,
+                ...getUpstreamTlsOptions(strictHttpsChecks),
                 ...clientCert,
                 ...caConfig
             }, (serverRes) => (async () => {
diff --git a/src/rules/websockets/websocket-handlers.ts b/src/rules/websockets/websocket-handlers.ts
index 41108a6c2..973ce184a 100644
--- a/src/rules/websockets/websocket-handlers.ts
+++ b/src/rules/websockets/websocket-handlers.ts
@@ -37,7 +37,7 @@ import { getAgent } from '../http-agents';
 import { ProxySettingSource } from '../proxy-config';
 import { assertParamDereferenced, RuleParameters } from '../rule-parameters';
 import {
-    UPSTREAM_TLS_OPTIONS,
+    getUpstreamTlsOptions,
     getClientRelativeHostname,
     getDnsLookupFunction,
     shouldUseStrictHttps
@@ -375,10 +375,7 @@ export class PassThroughWebSocketHandler extends PassThroughWebSocketHandlerDefi
             ) as { [key: string]: string }, // Simplify to string - doesn't matter though, only used by http module anyway
 
             // TLS options:
-            ...UPSTREAM_TLS_OPTIONS,
-            // Allow TLSv1, if !strict:
-            minVersion: strictHttpsChecks ? tls.DEFAULT_MIN_VERSION : 'TLSv1',
-            rejectUnauthorized: strictHttpsChecks,
+            ...getUpstreamTlsOptions(strictHttpsChecks),
             ...clientCert,
             ...caConfig
         } as WebSocket.ClientOptions & { lookup: any, maxPayload: number });