diff --git a/quarkus/config-api/src/main/java/org/keycloak/config/HttpOptions.java b/quarkus/config-api/src/main/java/org/keycloak/config/HttpOptions.java
index 4641000d54..09451ee3dd 100644
--- a/quarkus/config-api/src/main/java/org/keycloak/config/HttpOptions.java
+++ b/quarkus/config-api/src/main/java/org/keycloak/config/HttpOptions.java
@@ -59,12 +59,12 @@ public class HttpOptions {
             .defaultValue("TLSv1.3,TLSv1.2")
             .build();
 
-    public static final Option HTTPS_CERTIFICATE_FILE = new OptionBuilder<>("https-certificate-file", File.class)
+    public static final Option<File> HTTPS_CERTIFICATE_FILE = new OptionBuilder<>("https-certificate-file", File.class)
             .category(OptionCategory.HTTP)
             .description("The file path to a server certificate or certificate chain in PEM format.")
             .build();
 
-    public static final Option HTTPS_CERTIFICATE_KEY_FILE = new OptionBuilder<>("https-certificate-key-file", File.class)
+    public static final Option<File> HTTPS_CERTIFICATE_KEY_FILE = new OptionBuilder<>("https-certificate-key-file", File.class)
             .category(OptionCategory.HTTP)
             .description("The file path to a private key in PEM format.")
             .build();
diff --git a/quarkus/runtime/src/main/java/org/keycloak/quarkus/runtime/configuration/mappers/HttpPropertyMappers.java b/quarkus/runtime/src/main/java/org/keycloak/quarkus/runtime/configuration/mappers/HttpPropertyMappers.java
index ee7914f794..c1cb23be1a 100644
--- a/quarkus/runtime/src/main/java/org/keycloak/quarkus/runtime/configuration/mappers/HttpPropertyMappers.java
+++ b/quarkus/runtime/src/main/java/org/keycloak/quarkus/runtime/configuration/mappers/HttpPropertyMappers.java
@@ -13,6 +13,7 @@ import org.keycloak.quarkus.runtime.configuration.MicroProfileConfigProvider;
 import java.io.File;
 import java.nio.file.Paths;
 import java.util.Optional;
+import java.util.function.BiFunction;
 
 import static java.util.Optional.empty;
 import static java.util.Optional.of;
@@ -21,6 +22,8 @@ import static org.keycloak.quarkus.runtime.configuration.mappers.PropertyMappers
 import static org.keycloak.quarkus.runtime.integration.QuarkusPlatform.addInitializationException;
 
 final class HttpPropertyMappers {
+    private static final String QUARKUS_HTTPS_CERT_FILES = "quarkus.http.ssl.certificate.files";
+    private static final String QUARKUS_HTTPS_CERT_KEY_FILES = "quarkus.http.ssl.certificate.key-files";
 
     private HttpPropertyMappers(){}
 
@@ -64,15 +67,17 @@ final class HttpPropertyMappers {
                         .paramLabel("protocols")
                         .build(),
                 fromOption(HttpOptions.HTTPS_CERTIFICATE_FILE)
-                        .to("quarkus.http.ssl.certificate.files")
+                        .to(QUARKUS_HTTPS_CERT_FILES)
+                        .transformer(HttpPropertyMappers.validatePath(QUARKUS_HTTPS_CERT_FILES))
                         .paramLabel("file")
                         .build(),
                 fromOption(HttpOptions.HTTPS_CERTIFICATE_KEY_FILE)
-                        .to("quarkus.http.ssl.certificate.key-files")
+                        .to(QUARKUS_HTTPS_CERT_KEY_FILES)
+                        .transformer(HttpPropertyMappers.validatePath(QUARKUS_HTTPS_CERT_KEY_FILES))
                         .paramLabel("file")
                         .build(),
                 fromOption(HttpOptions.HTTPS_KEY_STORE_FILE
-                            .withRuntimeSpecificDefault(getDefaultKeystorePathValue()))
+                        .withRuntimeSpecificDefault(getDefaultKeystorePathValue()))
                         .to("quarkus.http.ssl.certificate.key-store-file")
                         .paramLabel("file")
                         .build(),
@@ -109,6 +114,10 @@ final class HttpPropertyMappers {
         };
     }
 
+    private static BiFunction<Optional<String>, ConfigSourceInterceptorContext, Optional<String>> validatePath(String key) {
+        return (value, context) -> Environment.isWindows() ? value.filter(v -> v.equals(context.proceed(key).getValue())).map(p -> p.replace("\\", "/")) : value;
+    }
+
     private static Optional<String> getHttpEnabledTransformer(Optional<String> value, ConfigSourceInterceptorContext context) {
         boolean enabled = Boolean.parseBoolean(value.get());
         ConfigValue proxy = context.proceed(MicroProfileConfigProvider.NS_KEYCLOAK_PREFIX + "proxy");
diff --git a/quarkus/tests/integration/src/test/java/org/keycloak/it/cli/dist/QuarkusPropertiesDistTest.java b/quarkus/tests/integration/src/test/java/org/keycloak/it/cli/dist/QuarkusPropertiesDistTest.java
index af2a5c2ace..e94f7ec782 100644
--- a/quarkus/tests/integration/src/test/java/org/keycloak/it/cli/dist/QuarkusPropertiesDistTest.java
+++ b/quarkus/tests/integration/src/test/java/org/keycloak/it/cli/dist/QuarkusPropertiesDistTest.java
@@ -28,6 +28,8 @@ import org.junit.jupiter.api.MethodOrderer.OrderAnnotation;
 import org.junit.jupiter.api.Order;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.TestMethodOrder;
+import org.junit.jupiter.api.condition.DisabledOnOs;
+import org.junit.jupiter.api.condition.OS;
 import org.keycloak.it.junit5.extension.BeforeStartDistribution;
 import org.keycloak.it.junit5.extension.CLIResult;
 import org.keycloak.it.junit5.extension.DistributionTest;
@@ -105,7 +107,7 @@ public class QuarkusPropertiesDistTest {
     @Test
     @BeforeStartDistribution(UpdateHibernateMetricsFromQuarkusProps.class)
     @Launch({ "build", "--metrics-enabled=true" })
-    @Order(8)
+    @Order(7)
     void buildFirstWithUnknownQuarkusBuildProperty(LaunchResult result) {
         CLIResult cliResult = (CLIResult) result;
         cliResult.assertBuild();
@@ -114,7 +116,7 @@ public class QuarkusPropertiesDistTest {
     @Test
     @KeepServerAlive
     @Launch({ "start", "--http-enabled=true", "--hostname-strict=false", OPTIMIZED_BUILD_OPTION_LONG})
-    @Order(9)
+    @Order(8)
     void testUnknownQuarkusBuildTimePropertyApplied(LaunchResult result) {
         CLIResult cliResult = (CLIResult) result;
         cliResult.assertNoBuild();
@@ -124,7 +126,7 @@ public class QuarkusPropertiesDistTest {
 
     @Test
     @Launch({ "start", "--http-enabled=true", "--hostname-strict=false", "--config-keystore=../../../../src/test/resources/keystore" })
-    @Order(10)
+    @Order(9)
     void testMissingSmallRyeKeyStorePasswordProperty(LaunchResult result) {
         CLIResult cliResult = (CLIResult) result;
         cliResult.assertError("config-keystore-password must be specified");
@@ -133,7 +135,7 @@ public class QuarkusPropertiesDistTest {
 
     @Test
     @Launch({ "start", "--http-enabled=true", "--hostname-strict=false", "--config-keystore-password=secret" })
-    @Order(11)
+    @Order(10)
     void testMissingSmallRyeKeyStorePathProperty(LaunchResult result) {
         CLIResult cliResult = (CLIResult) result;
         cliResult.assertError("config-keystore must be specified");
@@ -143,7 +145,7 @@ public class QuarkusPropertiesDistTest {
     @Test
     @Launch({ "start", "--http-enabled=true", "--hostname-strict=false", "--config-keystore=/invalid/path",
             "--config-keystore-password=secret" })
-    @Order(12)
+    @Order(11)
     void testInvalidSmallRyeKeyStorePathProperty(LaunchResult result) {
         CLIResult cliResult = (CLIResult) result;
         cliResult.assertError("java.lang.IllegalArgumentException: config-keystore path does not exist: /invalid/path");
@@ -153,7 +155,7 @@ public class QuarkusPropertiesDistTest {
     @Test
     @Launch({ "start", "--http-enabled=true", "--hostname-strict=false",
             "--config-keystore=../../../../src/test/resources/keystore", "--config-keystore-password=secret" })
-    @Order(13)
+    @Order(12)
     void testSmallRyeKeyStoreConfigSource(LaunchResult result) {
         // keytool -importpass -alias kc.log-level -keystore keystore -storepass secret -storetype PKCS12 -v (with "debug" as the stored password)
         CLIResult cliResult = (CLIResult) result;
@@ -161,6 +163,30 @@ public class QuarkusPropertiesDistTest {
         cliResult.assertBuild();
     }
 
+    @Test
+    @BeforeStartDistribution(ForceRebuild.class)
+    @DisabledOnOs(value = { OS.WINDOWS }, disabledReason = "Windows uses a different path separator.")
+    @Launch({ "start", "--http-enabled=true", "--hostname-strict=false",
+            "--https-certificate-file=/tmp/kc/bin/../conf/server.crt.pem",
+            "--https-certificate-key-file=/tmp/kc/bin/../conf/server.key.pem" })
+    @Order(13)
+    void testHttpCertsPathTransformer(LaunchResult result) {
+        CLIResult cliResult = (CLIResult) result;
+        assertTrue(cliResult.getOutput().contains("ERROR: /tmp/kc/bin/../conf/server.crt.pem"));
+    }
+
+    @Test
+    @BeforeStartDistribution(ForceRebuild.class)
+    @DisabledOnOs(value = { OS.LINUX, OS.MAC }, disabledReason = "Windows uses a different path separator.")
+    @Launch({ "start", "--http-enabled=true", "--hostname-strict=false",
+            "--https-certificate-file=C:\\tmp\\kc\\bin\\..\\conf/server.crt.pem",
+            "--https-certificate-key-file=C:\\tmp\\kc\\bin\\..\\conf/server.key.pem" })
+    @Order(14)
+    void testHttpCertsPathTransformerOnWindows(LaunchResult result) {
+        CLIResult cliResult = (CLIResult) result;
+        assertTrue(cliResult.getOutput().contains("ERROR: C:/tmp/kc/bin/../conf/server.crt.pem"));
+    }
+
     public static class UpdateConsoleLogLevelToWarnFromQuarkusProps implements Consumer<KeycloakDistribution> {
         @Override
         public void accept(KeycloakDistribution distribution) {
@@ -194,4 +220,13 @@ public class QuarkusPropertiesDistTest {
             distribution.setQuarkusProperty(QUARKUS_BUILDTIME_HIBERNATE_METRICS_KEY, "true");
         }
     }
+
+    public static class ForceRebuild implements Consumer<KeycloakDistribution> {
+
+        @Override
+        public void accept(KeycloakDistribution distribution) {
+            CLIResult buildResult = distribution.run("build");
+            buildResult.assertBuild();
+        }
+    }
 }
\ No newline at end of file