diff --git src/compiler/crystal/codegen/link.cr src/compiler/crystal/codegen/link.cr
index 4caf0060c..d7b9b19ca 100644
--- src/compiler/crystal/codegen/link.cr
+++ src/compiler/crystal/codegen/link.cr
@@ -136,7 +136,7 @@ module Crystal
       static_build = has_flag?("static")
 
       # Instruct the linker to link statically if the user asks
-      flags << "-static" if static_build
+      flags << "-static" if static_build && !has_flag?("darwin")
 
       # Add CRYSTAL_LIBRARY_PATH locations, so the linker preferentially
       # searches user-given library paths.
@@ -164,7 +164,32 @@ module Crystal
         end
       end
 
-      flags.join(" ")
+      process_flags(flags.join(" "))
+    end
+
+    private def process_flags(flags)
+      return flags if !(has_flag?("darwin") && has_flag?("static"))
+      # From `man 3 intro`
+      system_libs = ["c", "dbm", "dl", "info", "m", "poll", "pthread", "rpcsvc"]
+      new_flags = [] of String
+      flags.split.each do |flag|
+        if (lib_name = flag.lchop?("-l"))
+          static_lib = find_static_lib(lib_name)
+          if (!static_lib && !system_libs.includes?(lib_name))
+            Crystal.error "could not find lib#{lib_name}.a", 1
+          end
+          flag = static_lib if static_lib
+        end
+        new_flags << flag
+      end
+      new_flags.join(" ")
+    end
+
+    private def find_static_lib(libname)
+      CrystalLibraryPath.paths.each do |libdir|
+        static_lib = "#{libdir}/lib#{libname}.a"
+        return static_lib if File.exists?(static_lib)
+      end
     end
 
     PKG_CONFIG_PATH = Process.find_executable("pkg-config")
diff --git src/openssl/lib_crypto.cr src/openssl/lib_crypto.cr
index 77fc322ab..80005b0c3 100644
--- src/openssl/lib_crypto.cr
+++ src/openssl/lib_crypto.cr
@@ -26,7 +26,7 @@
   @[Link("crypt32")] # CertOpenStore, ...
   @[Link("user32")]  # GetProcessWindowStation, GetUserObjectInformationW, _MessageBoxW
 {% else %}
-  @[Link(ldflags: "`command -v pkg-config > /dev/null && pkg-config --libs --silence-errors libcrypto || printf %s '-lcrypto'`")]
+  @[Link("crypto", pkg_config: "libcrypto")]
 {% end %}
 lib LibCrypto
   alias Char = LibC::Char
diff --git src/openssl/lib_ssl.cr src/openssl/lib_ssl.cr
index f8c9d0908..cc961956a 100644
--- src/openssl/lib_ssl.cr
+++ src/openssl/lib_ssl.cr
@@ -33,7 +33,7 @@ require "./lib_crypto"
   @[Link("crypt32")] # CertOpenStore, ...
   @[Link("user32")]  # GetProcessWindowStation, GetUserObjectInformationW, _MessageBoxW
 {% else %}
-  @[Link(ldflags: "`command -v pkg-config > /dev/null && pkg-config --libs --silence-errors libssl || printf %s '-lssl -lcrypto'`")]
+  @[Link("ssl", pkg_config: "libssl")]
 {% end %}
 lib LibSSL
   alias Int = LibC::Int