diff --git a/pgpainless-cli/additional-native-metadata/._include-resources.json b/pgpainless-cli/additional-native-metadata/._include-resources.json
new file mode 100644
index 00000000..a9f75c28
Binary files /dev/null and b/pgpainless-cli/additional-native-metadata/._include-resources.json differ
diff --git a/pgpainless-cli/additional-native-metadata/._reflection.json b/pgpainless-cli/additional-native-metadata/._reflection.json
new file mode 100644
index 00000000..a9f75c28
Binary files /dev/null and b/pgpainless-cli/additional-native-metadata/._reflection.json differ
diff --git a/pgpainless-cli/additional-native-metadata/include-resources.json b/pgpainless-cli/additional-native-metadata/include-resources.json
new file mode 100644
index 00000000..42c2e3ce
--- /dev/null
+++ b/pgpainless-cli/additional-native-metadata/include-resources.json
@@ -0,0 +1,9 @@
+{
+  "resources": {
+    "includes": [
+      {
+        "pattern": "org/bouncycastle/.*"
+      }
+    ]
+  }
+}
diff --git a/pgpainless-cli/additional-native-metadata/reflection.json b/pgpainless-cli/additional-native-metadata/reflection.json
new file mode 100644
index 00000000..2e73df2a
--- /dev/null
+++ b/pgpainless-cli/additional-native-metadata/reflection.json
@@ -0,0 +1,17 @@
+[
+  {
+    "name" : "org.bouncycastle.jce.provider.BouncyCastleProvider",
+    "allDeclaredMethods" : true,
+    "allDeclaredConstructors" : true
+  },
+  {
+    "name" : "org.bouncycastle.openpgp.*",
+    "allDeclaredMethods" : true,
+    "allDeclaredConstructors" : true
+  },
+  {
+    "name": "org.bouncycastle.crypto.digests.SHA256Digest",
+    "allDeclaredConstructors": true,
+    "allDeclaredMethods": true
+  }
+]
diff --git a/pgpainless-cli/build.gradle b/pgpainless-cli/build.gradle
index 3d9a6a09..3c19c0e1 100644
--- a/pgpainless-cli/build.gradle
+++ b/pgpainless-cli/build.gradle
@@ -5,6 +5,7 @@
 plugins {
     id 'application'
     id "com.github.johnrengelman.shadow" version "6.1.0"
+    id 'org.graalvm.buildtools.native' version '0.10.3'
 }
 def generatedVersionDir = "${buildDir}/generated-version"
 
@@ -78,4 +79,28 @@ run {
     }
 }
 
+graalvmNative {
+    binaries {
+        main {
+            imageName = "GraalVM-Native-pgpainless"
+            mainClass = "$mainClassName"
+            buildArgs.add("-O4")
+            buildArgs.add('-H:ConfigurationFileDirectories=../../../build/resources/main/META-INF/native-image/')
+            buildArgs.add('--no-fallback')
+            buildArgs.add('--verbose')
+            buildArgs.add('-H:+BuildReport')
+            buildArgs.add('-J-XshowSettings:vm')
+            buildArgs.add('--report-unsupported-elements-at-runtime')
+            buildArgs.add('-H:+ReportExceptionStackTraces')
+            buildArgs.add('--initialize-at-build-time=org.bouncycastle')
+            buildArgs.add('--initialize-at-build-time=org.bouncycastle.jce.provider.BouncyCastleProvider')
+            buildArgs.add('-H:ReflectionConfigurationFiles=../../../additional-native-metadata/reflection.json')
+            buildArgs.add('-H:ResourceConfigurationFiles=../../../additional-native-metadata/include-resources.json')
+        }
+    }
+    binaries.all {
+        buildArgs.add("--verbose")
+    }
+}
+
 // tasks."jar".dependsOn(":pgpainless-core:assemble", ":pgpainless-sop:assemble")