diff --git a/Makefile b/Makefile
index a1d13e9..78102c6 100644
--- a/Makefile
+++ b/Makefile
@@ -18,8 +18,13 @@
 # - OpenSSL         - build OpenSSL for all platforms
 # - OpenSSL-macOS   - build OpenSSL for macOS
 # - OpenSSL-iOS     - build OpenSSL for iOS
+# - OpenSSL-iOS-simulator     - build OpenSSL for iOS-simulator
 # - OpenSSL-tvOS    - build OpenSSL for tvOS
+# - OpenSSL-tvOS-simulator    - build OpenSSL for tvOS-simulator
 # - OpenSSL-watchOS - build OpenSSL for watchOS
+# - OpenSSL-watchOS-simulator - build OpenSSL for watchOS-simulator
+# - OpenSSL-xrOS - build OpenSSL for xrOS (visionOS)
+# - OpenSSL-xrOS-simulator - build OpenSSL for xrOS-simulator
 # - libFFI          - build libFFI for all platforms (except macOS)
 # - libFFI-iOS      - build libFFI for iOS
 # - libFFI-tvOS     - build libFFI for tvOS
@@ -50,7 +55,7 @@ XZ_VERSION=5.4.2
 # Preference is to use OpenSSL 3; however, Cryptography 3.4.8 (and
 # probably some other packages as well) only works with 1.1.1, so
 # we need to preserve the ability to build the older OpenSSL (for now...)
-OPENSSL_VERSION=3.1.0
+OPENSSL_VERSION=3.1.1
 # OPENSSL_VERSION_NUMBER=1.1.1
 # OPENSSL_REVISION=q
 # OPENSSL_VERSION=$(OPENSSL_VERSION_NUMBER)$(OPENSSL_REVISION)
@@ -59,7 +64,7 @@ LIBFFI_VERSION=3.4.2
 
 # Supported OS and dependencies
 DEPENDENCIES=BZip2 XZ OpenSSL libFFI
-OS_LIST=macOS iOS tvOS watchOS
+OS_LIST=macOS iOS iOS-simulator tvOS tvOS-simulator watchOS watchOS-simulator xrOS xrOS-simulator
 
 CURL_FLAGS=--disable --fail --location --create-dirs --progress-bar
 
@@ -69,22 +74,41 @@ VERSION_MIN-macOS=10.15
 CFLAGS-macOS=-mmacosx-version-min=$(VERSION_MIN-macOS)
 
 # iOS targets
-TARGETS-iOS=iphonesimulator.x86_64 iphonesimulator.arm64 iphoneos.arm64
+TARGETS-iOS=iphoneos.arm64
 VERSION_MIN-iOS=12.0
 CFLAGS-iOS=-mios-version-min=$(VERSION_MIN-iOS)
 
+# iOS-simulator targets
+TARGETS-iOS-simulator=iphonesimulator.x86_64 iphonesimulator.arm64
+CFLAGS-iOS-simulator=-mios-simulator-version-min=$(VERSION_MIN-iOS)
+
 # tvOS targets
-TARGETS-tvOS=appletvsimulator.x86_64 appletvsimulator.arm64 appletvos.arm64
+TARGETS-tvOS=appletvos.arm64
 VERSION_MIN-tvOS=9.0
 CFLAGS-tvOS=-mtvos-version-min=$(VERSION_MIN-tvOS)
 PYTHON_CONFIGURE-tvOS=ac_cv_func_sigaltstack=no
 
+# tvOS-simulator targets
+TARGETS-tvOS-simulator=appletvsimulator.x86_64 appletvsimulator.arm64
+CFLAGS-tvOS-simulator=-mtvos-simulator-version-min=$(VERSION_MIN-tvOS)
+
 # watchOS targets
-TARGETS-watchOS=watchsimulator.x86_64 watchsimulator.arm64 watchos.arm64_32
+TARGETS-watchOS=watchos.armv7k watchos.arm64_32 watchos.arm64
 VERSION_MIN-watchOS=4.0
 CFLAGS-watchOS=-mwatchos-version-min=$(VERSION_MIN-watchOS)
 PYTHON_CONFIGURE-watchOS=ac_cv_func_sigaltstack=no
 
+# watchOS-simulator targets
+TARGETS-watchOS-simulator=watchsimulator.i386 watchsimulator.x86_64 watchsimulator.arm64
+CFLAGS-watchOS-simulator=-mwatchos-simulator-version-min=$(VERSION_MIN-watchOS)
+
+# xrOS targets
+TARGETS-xrOS=xros.arm64
+PYTHON_CONFIGURE-xrOS=ac_cv_func_sigaltstack=no
+
+# xrOS-simulator targets
+TARGETS-xrOS-simulator=xrsimulator.x86_64 xrsimulator.arm64
+
 # The architecture of the machine doing the build
 HOST_ARCH=$(shell uname -m)
 HOST_PYTHON=install/macOS/macosx/python-$(PYTHON_VERSION)
@@ -662,7 +686,7 @@ BZIP2_FATLIB-$(sdk)=$$(BZIP2_MERGE-$(sdk))/lib/libbz2.a
 XZ_MERGE-$(sdk)=$(PROJECT_DIR)/merge/$(os)/$(sdk)/xz-$(XZ_VERSION)
 XZ_FATLIB-$(sdk)=$$(XZ_MERGE-$(sdk))/lib/liblzma.a
 
-OPENSSL_MERGE-$(sdk)=$(PROJECT_DIR)/merge/$(os)/$(sdk)/openssl-$(OPENSSL_VERSION)
+OPENSSL_MERGE-$(sdk)=$(PROJECT_DIR)/merge/$(os)/openssl
 OPENSSL_FATINCLUDE-$(sdk)=$$(OPENSSL_MERGE-$(sdk))/include
 OPENSSL_SSL_FATLIB-$(sdk)=$$(OPENSSL_MERGE-$(sdk))/lib/libssl.a
 OPENSSL_CRYPTO_FATLIB-$(sdk)=$$(OPENSSL_MERGE-$(sdk))/lib/libcrypto.a
@@ -716,14 +740,14 @@ $$(OPENSSL_SSL_FATLIB-$(sdk)): $$(foreach target,$$(SDK_TARGETS-$(sdk)),$$(OPENS
 	mkdir -p $$(OPENSSL_MERGE-$(sdk))/lib
 	lipo -create -output $$@ \
 		$$(foreach target,$$(SDK_TARGETS-$(sdk)),$$(OPENSSL_SSL_LIB-$$(target))) \
-		2>&1 | tee -a merge/$(os)/$(sdk)/openssl-$(OPENSSL_VERSION).ssl.lipo.log
+		2>&1 | tee -a merge/$(os)/openssl-$(OPENSSL_VERSION).ssl.lipo.log
 
 $$(OPENSSL_CRYPTO_FATLIB-$(sdk)): $$(foreach target,$$(SDK_TARGETS-$(sdk)),$$(OPENSSL_CRYPTO_LIB-$$(target)))
 	@echo ">>> Build OpenSSL crypto fat library for $(sdk)"
 	mkdir -p $$(OPENSSL_MERGE-$(sdk))/lib
 	lipo -create -output $$@ \
 		$$(foreach target,$$(SDK_TARGETS-$(sdk)),$$(OPENSSL_CRYPTO_LIB-$$(target))) \
-		2>&1 | tee -a merge/$(os)/$(sdk)/openssl-$(OPENSSL_VERSION).crypto.lipo.log
+		2>&1 | tee -a merge/$(os)/openssl-$(OPENSSL_VERSION).crypto.lipo.log
 
 ###########################################################################
 # SDK: libFFI