diff --git a/api/build.gradle.kts b/api/build.gradle.kts
index d3e55559f..6c99ac61e 100644
--- a/api/build.gradle.kts
+++ b/api/build.gradle.kts
@@ -39,7 +39,7 @@ dependencies {
     api(libs.guice)
     api(libs.checker.qual)
     api(libs.brigadier)
-    api(libs.bundles.configurate)
+    api(libs.bundles.configurate4)
     api(libs.caffeine)
 }
 
@@ -60,17 +60,12 @@ tasks {
             "https://www.slf4j.org/apidocs/",
             "https://guava.dev/releases/${libs.guava.get().version}/api/docs/",
             "https://google.github.io/guice/api-docs/${libs.guice.get().version}/javadoc/",
-            "https://docs.oracle.com/en/java/javase/11/docs/api/",
+            "https://docs.oracle.com/en/java/javase/17/docs/api/",
             "https://jd.advntr.dev/api/${libs.adventure.bom.get().version}/",
             "https://javadoc.io/doc/com.github.ben-manes.caffeine/caffeine"
         )
 
         // Disable the crazy super-strict doclint tool in Java 8
         o.addStringOption("Xdoclint:none", "-quiet")
-
-        // Remove "undefined" from search paths when generating javadoc for a non-modular project (JDK-8215291)
-        if (JavaVersion.current() >= JavaVersion.VERSION_1_9 && JavaVersion.current() < JavaVersion.VERSION_12) {
-            o.addBooleanOption("-no-module-directories", true)
-        }
     }
 }
diff --git a/gradle/libs.versions.toml b/gradle/libs.versions.toml
index df4fb54db..4ccf52cda 100644
--- a/gradle/libs.versions.toml
+++ b/gradle/libs.versions.toml
@@ -1,5 +1,6 @@
 [versions]
-configurate = "3.7.3"
+configurate3 = "3.7.3"
+configurate4 = "4.1.2"
 flare = "2.0.1"
 log4j = "2.20.0"
 netty = "4.1.100.Final"
@@ -20,9 +21,12 @@ caffeine = "com.github.ben-manes.caffeine:caffeine:3.1.5"
 checker-qual = "org.checkerframework:checker-qual:3.28.0"
 checkstyle = "com.puppycrawl.tools:checkstyle:10.9.3"
 completablefutures = "com.spotify:completable-futures:0.3.5"
-configurate-hocon = { module = "org.spongepowered:configurate-hocon", version.ref = "configurate" }
-configurate-yaml = { module = "org.spongepowered:configurate-yaml", version.ref = "configurate" }
-configurate-gson = { module = "org.spongepowered:configurate-gson", version.ref = "configurate" }
+configurate3-hocon = { module = "org.spongepowered:configurate-hocon", version.ref = "configurate3" }
+configurate3-yaml = { module = "org.spongepowered:configurate-yaml", version.ref = "configurate3" }
+configurate3-gson = { module = "org.spongepowered:configurate-gson", version.ref = "configurate3" }
+configurate4-hocon = { module = "org.spongepowered:configurate-hocon", version.ref = "configurate4" }
+configurate4-yaml = { module = "org.spongepowered:configurate-yaml", version.ref = "configurate4" }
+configurate4-gson = { module = "org.spongepowered:configurate-gson", version.ref = "configurate4" }
 disruptor = "com.lmax:disruptor:3.4.4"
 fastutil = "it.unimi.dsi:fastutil:8.5.12"
 flare-core = { module = "space.vectrix.flare:flare", version.ref = "flare" }
@@ -54,6 +58,7 @@ spotbugs-annotations = "com.github.spotbugs:spotbugs-annotations:4.7.3"
 terminalconsoleappender = "net.minecrell:terminalconsoleappender:1.3.0"
 
 [bundles]
-configurate = ["configurate-hocon", "configurate-yaml", "configurate-gson"]
+configurate3 = ["configurate3-hocon", "configurate3-yaml", "configurate3-gson"]
+configurate4 = ["configurate4-hocon", "configurate4-yaml", "configurate4-gson"]
 flare = ["flare-core", "flare-fastutil"]
 log4j = ["log4j-api", "log4j-core", "log4j-slf4j-impl", "log4j-iostreams", "log4j-jul"]
diff --git a/gradle/wrapper/gradle-wrapper.jar b/gradle/wrapper/gradle-wrapper.jar
index ccebba771..d64cd4917 100644
Binary files a/gradle/wrapper/gradle-wrapper.jar and b/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/gradle/wrapper/gradle-wrapper.properties b/gradle/wrapper/gradle-wrapper.properties
index 0c85a1f75..1af9e0930 100644
--- a/gradle/wrapper/gradle-wrapper.properties
+++ b/gradle/wrapper/gradle-wrapper.properties
@@ -1,6 +1,7 @@
 distributionBase=GRADLE_USER_HOME
 distributionPath=wrapper/dists
-distributionUrl=https\://services.gradle.org/distributions/gradle-8.1-bin.zip
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.5-bin.zip
 networkTimeout=10000
+validateDistributionUrl=true
 zipStoreBase=GRADLE_USER_HOME
 zipStorePath=wrapper/dists
diff --git a/gradlew b/gradlew
index 79a61d421..1aa94a426 100755
--- a/gradlew
+++ b/gradlew
@@ -83,10 +83,8 @@ done
 # This is normally unused
 # shellcheck disable=SC2034
 APP_BASE_NAME=${0##*/}
-APP_HOME=$( cd "${APP_HOME:-./}" && pwd -P ) || exit
-
-# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
-DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+# Discard cd standard output in case $CDPATH is set (https://github.com/gradle/gradle/issues/25036)
+APP_HOME=$( cd "${APP_HOME:-./}" > /dev/null && pwd -P ) || exit
 
 # Use the maximum available, or set MAX_FD != -1 to use that value.
 MAX_FD=maximum
@@ -133,10 +131,13 @@ location of your Java installation."
     fi
 else
     JAVACMD=java
-    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+    if ! command -v java >/dev/null 2>&1
+    then
+        die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
 
 Please set the JAVA_HOME variable in your environment to match the
 location of your Java installation."
+    fi
 fi
 
 # Increase the maximum file descriptors if we can.
@@ -144,7 +145,7 @@ if ! "$cygwin" && ! "$darwin" && ! "$nonstop" ; then
     case $MAX_FD in #(
       max*)
         # In POSIX sh, ulimit -H is undefined. That's why the result is checked to see if it worked.
-        # shellcheck disable=SC3045
+        # shellcheck disable=SC2039,SC3045
         MAX_FD=$( ulimit -H -n ) ||
             warn "Could not query maximum file descriptor limit"
     esac
@@ -152,7 +153,7 @@ if ! "$cygwin" && ! "$darwin" && ! "$nonstop" ; then
       '' | soft) :;; #(
       *)
         # In POSIX sh, ulimit -n is undefined. That's why the result is checked to see if it worked.
-        # shellcheck disable=SC3045
+        # shellcheck disable=SC2039,SC3045
         ulimit -n "$MAX_FD" ||
             warn "Could not set maximum file descriptor limit to $MAX_FD"
     esac
@@ -197,11 +198,15 @@ if "$cygwin" || "$msys" ; then
     done
 fi
 
-# Collect all arguments for the java command;
-#   * $DEFAULT_JVM_OPTS, $JAVA_OPTS, and $GRADLE_OPTS can contain fragments of
-#     shell script including quotes and variable substitutions, so put them in
-#     double quotes to make sure that they get re-expanded; and
-#   * put everything else in single quotes, so that it's not re-expanded.
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Collect all arguments for the java command:
+#   * DEFAULT_JVM_OPTS, JAVA_OPTS, JAVA_OPTS, and optsEnvironmentVar are not allowed to contain shell fragments,
+#     and any embedded shellness will be escaped.
+#   * For example: A user cannot expect ${Hostname} to be expanded, as it is an environment variable and will be
+#     treated as '${Hostname}' itself on the command line.
 
 set -- \
         "-Dorg.gradle.appname=$APP_BASE_NAME" \
diff --git a/proxy/build.gradle.kts b/proxy/build.gradle.kts
index fd7042ecd..14eb4b19d 100644
--- a/proxy/build.gradle.kts
+++ b/proxy/build.gradle.kts
@@ -85,6 +85,11 @@ tasks {
         exclude("org/checkerframework/checker/**")
 
         relocate("org.bstats", "com.velocitypowered.proxy.bstats")
+
+        // Include Configurate 3
+        val configurateBuildTask = project(":deprecated-configurate3").tasks.named("shadowJar")
+        dependsOn(configurateBuildTask)
+        from(zipTree(configurateBuildTask.map { it.outputs.files.singleFile }))
     }
 }
 
diff --git a/proxy/deprecated/configurate3/build.gradle.kts b/proxy/deprecated/configurate3/build.gradle.kts
new file mode 100644
index 000000000..6a7d0daae
--- /dev/null
+++ b/proxy/deprecated/configurate3/build.gradle.kts
@@ -0,0 +1,13 @@
+plugins {
+    alias(libs.plugins.shadow)
+}
+
+dependencies {
+    implementation(libs.bundles.configurate3)
+}
+
+tasks.shadowJar {
+    exclude("com/google/**")
+    exclude("com/typesafe/**")
+    exclude("org/yaml/**")
+}
diff --git a/settings.gradle.kts b/settings.gradle.kts
index 0c31266f9..7b375a6f9 100644
--- a/settings.gradle.kts
+++ b/settings.gradle.kts
@@ -32,3 +32,7 @@ sequenceOf(
     include(project)
     project(project).projectDir = file(it)
 }
+
+val deprecatedConfigurateModule = ":deprecated-configurate3"
+include(deprecatedConfigurateModule)
+project(deprecatedConfigurateModule).projectDir = file("proxy/deprecated/configurate3")