diff --git a/Makefile b/Makefile
index 39c0bc11..ccf14c9d 100644
--- a/Makefile
+++ b/Makefile
@@ -12,7 +12,7 @@ BUILD_DIR ?= out
 UNAME_S := $(shell uname -s)
 UNAME_M := $(shell uname -m)
 ifeq ($(UNAME_S),Darwin)
-BUILD_TYPES := macosdebug macosrelease iosdebug iosrelease
+BUILD_TYPES := macosdebug macosrelease iosdebug iosrelease iossimdebug iossimrelease
 else
 BUILD_TYPES := debug release windebug winrelease androiddebug androidrelease androiddebug-x86 androidrelease-x86 androiddebug-x86_64 androidrelease-x86_64 androiddebug-armv7a androidrelease-armv7a
 endif
@@ -62,11 +62,15 @@ MACOS_TARGETS := \
 IOS_TARGETS := \
 	out/iosdebug/tildefriends \
 	out/iosrelease/tildefriends
+IOSSIM_TARGETS := \
+	out/iossimdebug/tildefriends \
+	out/iossimrelease/tildefriends
 
 DEBUG_TARGETS := \
 	out/debug/tildefriends \
 	out/windebug/tildefriends.exe \
 	out/iosdebug/tildefriends \
+	out/iossimdebug/tildefriends \
 	out/macosdebug/tildefriends \
 	out/androiddebug/tildefriends \
 	out/androiddebug-armv7a/tildefriends \
@@ -76,6 +80,7 @@ RELEASE_TARGETS := \
 	out/release/tildefriends \
 	out/winrelease/tildefriends.exe \
 	out/iosrelease/tildefriends \
+	out/iossimrelease/tildefriends \
 	out/macosrelease/tildefriends \
 	out/androidrelease/tildefriends \
 	out/androidrelease-armv7a/tildefriends \
@@ -84,7 +89,7 @@ RELEASE_TARGETS := \
 ANDROID_RELEASE_TARGETS := $(filter-out $(DEBUG_TARGETS),$(ANDROID_TARGETS))
 NONANDROID_RELEASE_TARGETS := $(filter-out $(ANDROID_ARM64_TARGETS),$(RELEASE_TARGETS))
 NONANDROID_TARGETS := $(filter-out $(ANDROID_TARGETS),$(DEBUG_TARGETS) $(RELEASE_TARGETS))
-NONMACOS_TARGETS := $(filter-out $(MACOS_TARGETS) $(IOS_TARGETS),$(DEBUG_TARGETS) $(RELEASE_TARGETS))
+NONMACOS_TARGETS := $(filter-out $(MACOS_TARGETS) $(IOS_TARGETS) $(IOSSIM_TARGETS),$(DEBUG_TARGETS) $(RELEASE_TARGETS))
 
 $(NONANDROID_TARGETS): CFLAGS += -fno-omit-frame-pointer
 $(filter-out $(ANDROID_TARGETS) $(WINDOWS_TARGETS),$(DEBUG_TARGETS) $(RELEASE_TARGETS)): LDFLAGS += -rdynamic
@@ -115,6 +120,8 @@ ifeq ($(UNAME_S),Darwin)
 $(MACOS_TARGETS): CC = xcrun clang
 $(IOS_TARGETS): IOS_SYSROOT := $(shell xcrun --sdk iphoneos --show-sdk-path)
 $(IOS_TARGETS): CC = xcrun --sdk iphoneos clang -isysroot $(IOS_SYSROOT) -arch arm64
+$(IOSSIM_TARGETS): IOSSIM_SYSROOT := $(shell xcrun --sdk iphonesimulator --show-sdk-path)
+$(IOSSIM_TARGETS): CC = xcrun --sdk iphonesimulator clang -isysroot $(IOSSIM_SYSROOT) -arch x86_64
 endif
 $(ANDROID_X86_64_TARGETS): ANDROID_NDK_TARGET_TRIPLE := x86_64-linux-android
 $(ANDROID_X86_TARGETS): ANDROID_NDK_TARGET_TRIPLE := i686-linux-android
@@ -138,6 +145,8 @@ $(NONMACOS_TARGETS): CFLAGS += -Wno-cast-function-type
 $(NONMACOS_TARGETS): LDFLAGS += -Wl,--gc-sections
 $(IOS_TARGETS): CFLAGS += -Ideps/openssl/ios/ios64-xcrun/usr/local/include
 $(IOS_TARGETS): LDFLAGS += -Ldeps/openssl/ios/ios64-xcrun/usr/local/lib
+$(IOSSIM_TARGETS): CFLAGS += -Ideps/openssl/ios/iossimulator-xcrun/usr/local/include
+$(IOSSIM_TARGETS): LDFLAGS += -Ldeps/openssl/ios/iossimulator-xcrun/usr/local/lib
 
 ifeq ($(UNAME_M),x86_64)
 debug: CFLAGS += -fsanitize=address -fsanitize=undefined -fno-common
@@ -150,7 +159,7 @@ get_objs = \
 	$(foreach build_type,windebug winrelease,$(addprefix $(BUILD_DIR)/$(build_type)/,$(addsuffix .o,$(basename $(value $(1)_win))))) \
 	$(foreach build_type,androiddebug androidrelease androiddebug-x86 androidrelease-x86 androiddebug-x86_64 androidrelease-x86_64 androiddebug-armv7a androiddebug-armv7a,$(addprefix $(BUILD_DIR)/$(build_type)/,$(addsuffix .o,$(basename $(value $(1)_android))))) \
 	$(foreach build_type,androiddebug androidrelease androiddebug-x86 androidrelease-x86 androiddebug-x86_64 androidrelease-x86_64 androiddebug-armv7a androidrelease-armv7a,$(addprefix $(BUILD_DIR)/$(build_type)/,$(addsuffix .o,$(basename $(value $(1)_unix))))) \
-	$(foreach build_type,macosdebug macosrelease iosdebug iosrelease,$(addprefix $(BUILD_DIR)/$(build_type)/,$(addsuffix .o,$(basename $(value $(1)_macos))))) \
+	$(foreach build_type,macosdebug macosrelease iosdebug iosrelease iossimdebug iossimrelease,$(addprefix $(BUILD_DIR)/$(build_type)/,$(addsuffix .o,$(basename $(value $(1)_macos))))) \
 	$(foreach build_type,androiddebug-x86 androidrelease-x86,$(addprefix $(BUILD_DIR)/$(build_type)/,$(addsuffix .o,$(basename $(value $(1)_x86)))))
 
 APP_SOURCES := $(wildcard src/*.c)
@@ -474,7 +483,7 @@ $(MINIUNZIP_OBJS): CFLAGS += \
 LDFLAGS += \
 	-pthread \
 	-lm
-debug release $(MACOS_TARGETS) $(IOS_TARGETS): LDFLAGS += \
+debug release $(MACOS_TARGETS) $(IOS_TARGETS) $(IOSSIM_TARGETS): LDFLAGS += \
 	-ldl \
 	-lssl \
 	-lcrypto
diff --git a/tools/ssl-ios b/tools/ssl-ios
index 43352425..ca0542c0 100755
--- a/tools/ssl-ios
+++ b/tools/ssl-ios
@@ -6,7 +6,7 @@ API_LEVEL=28
 
 BUILD_DIR=out/openssl_ios_build
 
-BUILD_TARGETS="ios64-xcrun"
+BUILD_TARGETS="ios64-xcrun iossimulator-xcrun"
 
 rm -rfv openssl-${OPENSSL_VERSION}
 
@@ -47,6 +47,13 @@ do
         SSL_TARGET="ios64-xcrun"
         CC=clang
     ;;
+    iossimulator-xcrun)
+        TRIBLE="x86_64-darwin-ios"
+        OPTIONS="--static -static -ffunction-sections -fdata-sections -fPIC -Wno-macro-redefined"
+        DESTDIR="/tmp/$BUILD_DIR/x86_64-iossim"
+        SSL_TARGET="iossimulator-xcrun"
+        CC=clang
+    ;;
     esac
 
     rm -rf $DESTDIR