diff --git a/deps.edn b/deps.edn
index d9ed180b..39325e38 100644
--- a/deps.edn
+++ b/deps.edn
@@ -30,7 +30,7 @@
         org.postgresql/postgresql {:mvn/version "42.2.18"}
         org.hsqldb/hsqldb {:mvn/version "2.5.1"}
         datascript/datascript {:mvn/version "1.0.1"}
-        http-kit/http-kit {:mvn/version "2.5.1"}
+        http-kit/http-kit {:mvn/version "2.5.3"}
         babashka/clojure-lanterna {:mvn/version "0.9.8-SNAPSHOT"}
         org.clojure/math.combinatorics {:mvn/version "0.1.6"}
         org.clojure/core.match {:mvn/version "1.0.0"}
diff --git a/project.clj b/project.clj
index b91000a0..8c3855f7 100644
--- a/project.clj
+++ b/project.clj
@@ -42,9 +42,9 @@
              :feature/datascript {:source-paths ["feature-datascript"]
                                   :dependencies [[datascript "1.0.1"]]}
              :feature/httpkit-client {:source-paths ["feature-httpkit-client"]
-                                      :dependencies [[http-kit "2.5.1"]]}
+                                      :dependencies [[http-kit "2.5.3"]]}
              :feature/httpkit-server {:source-paths ["feature-httpkit-server"]
-                                      :dependencies [[http-kit "2.5.1"]]}
+                                      :dependencies [[http-kit "2.5.3"]]}
              :feature/lanterna {:source-paths ["feature-lanterna"]
                                 :dependencies [[babashka/clojure-lanterna "0.9.8-SNAPSHOT"]]}
              :feature/core-match {:source-paths ["feature-core-match"]
diff --git a/script/compile b/script/compile
index 5451c4f6..da9d08a2 100755
--- a/script/compile
+++ b/script/compile
@@ -61,6 +61,7 @@ args=( "-jar" "$BABASHKA_JAR"
        "--no-server"
        "--report-unsupported-elements-at-runtime"
        "--initialize-at-run-time=org.postgresql.sspi.SSPIClient"
+       "--initialize-at-run-time=org.httpkit.client.ClientSslEngineFactory\$SSLHolder"
        "--native-image-info"
        "--verbose"
        "-H:ServiceLoaderFeatureExcludeServices=javax.sound.sampled.spi.AudioFileReader"
diff --git a/script/compile.bat b/script/compile.bat
index f0f13db2..7e62fa4e 100644
--- a/script/compile.bat
+++ b/script/compile.bat
@@ -34,6 +34,7 @@ call %GRAALVM_HOME%\bin\native-image.cmd ^
   "-H:ReflectionConfigurationFiles=reflection.json" ^
   "--initialize-at-build-time"  ^
   "--initialize-at-run-time=org.postgresql.sspi.SSPIClient" ^
+  "--initialize-at-run-time=org.httpkit.client.ClientSslEngineFactory\$SSLHolder" ^
   "-H:EnableURLProtocols=http,https,jar" ^
   "--enable-all-security-services" ^
   "-H:+JNI" ^