diff --git a/CHANGELOG.md b/CHANGELOG.md
index 145aff1..6c19983 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -12,6 +12,11 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - WireGuard support. [#236](https://github.com/passepartoutvpn/tunnelkit/pull/236)
 - Handle `--keepalive` option.
 
+### Changed
+
+- Relax deployment target for macOS down to 10.14
+- Upgrade OpenSSL to 1.1.1m.
+
 ## 4.0.3 (2021-11-27)
 
 ### Fixed
diff --git a/Demo/TunnelKit.xcodeproj/project.pbxproj b/Demo/TunnelKit.xcodeproj/project.pbxproj
index 64766fc..301bdf3 100644
--- a/Demo/TunnelKit.xcodeproj/project.pbxproj
+++ b/Demo/TunnelKit.xcodeproj/project.pbxproj
@@ -1117,7 +1117,7 @@
 				GCC_WARN_UNUSED_FUNCTION = YES;
 				GCC_WARN_UNUSED_VARIABLE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 12.0;
-				MACOSX_DEPLOYMENT_TARGET = 10.15;
+				MACOSX_DEPLOYMENT_TARGET = 10.14;
 				MTL_ENABLE_DEBUG_INFO = YES;
 				ONLY_ACTIVE_ARCH = YES;
 				PATH = "${PATH}:/opt/homebrew/bin";
@@ -1178,7 +1178,7 @@
 				GCC_WARN_UNUSED_FUNCTION = YES;
 				GCC_WARN_UNUSED_VARIABLE = YES;
 				IPHONEOS_DEPLOYMENT_TARGET = 12.0;
-				MACOSX_DEPLOYMENT_TARGET = 10.15;
+				MACOSX_DEPLOYMENT_TARGET = 10.14;
 				MTL_ENABLE_DEBUG_INFO = NO;
 				PATH = "${PATH}:/opt/homebrew/bin";
 				SDKROOT = iphoneos;
diff --git a/Package.resolved b/Package.resolved
index 34adf8e..6b0e273 100644
--- a/Package.resolved
+++ b/Package.resolved
@@ -6,8 +6,8 @@
         "repositoryURL": "https://github.com/passepartoutvpn/openssl-apple",
         "state": {
           "branch": null,
-          "revision": "42a049c406c1aa3df11a8dd14b1b11cd470f4a00",
-          "version": "1.1.11200"
+          "revision": "cbbff97a99384a5415bb47c072c376066b78f65f",
+          "version": "1.1.11300"
         }
       },
       {
diff --git a/Package.swift b/Package.swift
index 8bd26a3..ecdaeda 100644
--- a/Package.swift
+++ b/Package.swift
@@ -6,7 +6,7 @@ import PackageDescription
 let package = Package(
     name: "TunnelKit",
     platforms: [
-        .iOS(.v12), .macOS(.v10_15)
+        .iOS(.v12), .macOS(.v10_14)
     ],
     products: [
         // Products define the executables and libraries a package produces, and make them visible to other packages.
@@ -43,7 +43,7 @@ let package = Package(
         // Dependencies declare other packages that this package depends on.
         // .package(url: /* package url */, from: "1.0.0"),
         .package(url: "https://github.com/SwiftyBeaver/SwiftyBeaver", from: "1.9.0"),
-        .package(url: "https://github.com/passepartoutvpn/openssl-apple", from: "1.1.11200"),
+        .package(url: "https://github.com/passepartoutvpn/openssl-apple", from: "1.1.11300"),
         .package(name: "WireGuardKit", url: "https://git.zx2c4.com/wireguard-apple", .exact("1.0.15-26"))
     ],
     targets: [
diff --git a/README.md b/README.md
index faa11fe..546d121 100644
--- a/README.md
+++ b/README.md
@@ -1,5 +1,5 @@
 ![iOS 12+](https://img.shields.io/badge/ios-12+-green.svg)
-![macOS 10.15+](https://img.shields.io/badge/macos-10.15+-green.svg)
+![macOS 10.14+](https://img.shields.io/badge/macos-10.14+-green.svg)
 [![License GPLv3](https://img.shields.io/badge/license-GPLv3-lightgray.svg)](LICENSE)
 
 [![Unit Tests](https://github.com/passepartoutvpn/tunnelkit/actions/workflows/test.yml/badge.svg)](https://github.com/passepartoutvpn/tunnelkit/actions/workflows/test.yml)
@@ -100,7 +100,7 @@ Therefore, make sure to follow the steps below for proper integration:
 
 ### Requirements
 
-- iOS 12.0+ / macOS 10.15+
+- iOS 12.0+ / macOS 10.14+
 - SwiftPM 5.3
 - Git (preinstalled with Xcode Command Line Tools)
 
diff --git a/Sources/TunnelKitManager/Keychain.swift b/Sources/TunnelKitManager/Keychain.swift
index 4cc323f..67de376 100644
--- a/Sources/TunnelKitManager/Keychain.swift
+++ b/Sources/TunnelKitManager/Keychain.swift
@@ -321,7 +321,9 @@ public class Keychain {
         if let accessGroup = accessGroup {
             query[kSecAttrAccessGroup as String] = accessGroup
             #if os(macOS)
-            query[kSecUseDataProtectionKeychain as String] = true
+            if #available(macOS 10.15, *) {
+                query[kSecUseDataProtectionKeychain as String] = true
+            }
             #endif
         }
         if let context = context {