diff --git a/dd-java-agent/agent-bootstrap/agent-bootstrap.gradle b/dd-java-agent/agent-bootstrap/agent-bootstrap.gradle
index d7353bb842..eb60f16435 100644
--- a/dd-java-agent/agent-bootstrap/agent-bootstrap.gradle
+++ b/dd-java-agent/agent-bootstrap/agent-bootstrap.gradle
@@ -12,7 +12,3 @@ dependencies {
   compile group: 'org.slf4j', name: 'slf4j-simple', version: versions.slf4j
   // ^ Generally a bad idea for libraries, but we're shadowing.
 }
-
-jar {
-  classifier = 'unbundled'
-}
diff --git a/dd-java-agent/agent-jmxfetch/agent-jmxfetch.gradle b/dd-java-agent/agent-jmxfetch/agent-jmxfetch.gradle
index 37a8c2d659..bee388bec6 100644
--- a/dd-java-agent/agent-jmxfetch/agent-jmxfetch.gradle
+++ b/dd-java-agent/agent-jmxfetch/agent-jmxfetch.gradle
@@ -27,10 +27,6 @@ shadowJar {
   }
 }
 
-jar {
-  classifier = 'unbundled'
-}
-
 tasks.register("submodulesUpdate", Exec) {
   group 'Build Setup'
   description 'Initializes and updates integrations-core git submodule'
diff --git a/dd-java-agent/benchmark/benchmark.gradle b/dd-java-agent/benchmark/benchmark.gradle
index b87e238478..8d0205b087 100644
--- a/dd-java-agent/benchmark/benchmark.gradle
+++ b/dd-java-agent/benchmark/benchmark.gradle
@@ -1,5 +1,5 @@
 plugins {
-  id "me.champeau.gradle.jmh" version "0.4.8"
+  id "me.champeau.gradle.jmh" version "0.5.0"
 }
 
 apply from: "${rootDir}/gradle/java.gradle"
diff --git a/dd-java-agent/dd-java-agent.gradle b/dd-java-agent/dd-java-agent.gradle
index 95f7895f0f..a3229e9900 100644
--- a/dd-java-agent/dd-java-agent.gradle
+++ b/dd-java-agent/dd-java-agent.gradle
@@ -1,5 +1,5 @@
 plugins {
-  id "com.github.johnrengelman.shadow" version "4.0.4"
+  id "com.github.johnrengelman.shadow" version "5.2.0"
 }
 
 description = 'dd-java-agent'
@@ -20,7 +20,7 @@ def includeShadowJar(subproject, jarname) {
   def agent_project = project
   subproject.afterEvaluate {
     agent_project.processResources {
-      from(zipTree(subproject.tasks.shadowJar.archivePath)) {
+      from(zipTree(subproject.tasks.shadowJar.archiveFile)) {
         into jarname
         rename '(^.*)\\.class$', '$1.classdata'
         // Rename LICENSE file since it clashes with license dir on non-case sensitive FSs (i.e. Mac)
@@ -30,8 +30,6 @@ def includeShadowJar(subproject, jarname) {
 
     agent_project.processResources.dependsOn subproject.tasks.shadowJar
     subproject.shadowJar {
-      classifier null
-
       mergeServiceFiles()
 
       exclude '**/module-info.class'
@@ -58,7 +56,7 @@ includeShadowJar(project(':dd-java-agent:instrumentation'), 'agent-tooling-and-i
 includeShadowJar(project(':dd-java-agent:agent-jmxfetch'), 'agent-jmxfetch.isolated')
 
 jar {
-  classifier = 'unbundled'
+  archiveClassifier = 'unbundled'
 
   manifest {
     attributes(
@@ -74,7 +72,7 @@ jar {
 shadowJar {
   configurations = [project.configurations.shadowInclude]
 
-  classifier null
+  archiveClassifier = ''
 
   mergeServiceFiles()
 
@@ -111,7 +109,7 @@ dependencies {
   testCompile deps.testLogging
   testCompile deps.guava
 
-  shadowInclude project(':dd-java-agent:agent-bootstrap')
+  shadowInclude project(path: ':dd-java-agent:agent-bootstrap')
 }
 
 tasks.withType(Test).configureEach {
diff --git a/dd-java-agent/instrumentation/grpc-1.5/grpc-1.5.gradle b/dd-java-agent/instrumentation/grpc-1.5/grpc-1.5.gradle
index bdfa0b6b52..4141e1c519 100644
--- a/dd-java-agent/instrumentation/grpc-1.5/grpc-1.5.gradle
+++ b/dd-java-agent/instrumentation/grpc-1.5/grpc-1.5.gradle
@@ -11,7 +11,7 @@ buildscript {
     mavenCentral()
   }
   dependencies {
-    classpath 'com.google.protobuf:protobuf-gradle-plugin:0.8.6'
+    classpath 'com.google.protobuf:protobuf-gradle-plugin:0.8.10'
   }
 }
 
diff --git a/dd-java-agent/instrumentation/instrumentation.gradle b/dd-java-agent/instrumentation/instrumentation.gradle
index 56e720de18..c252a05e67 100644
--- a/dd-java-agent/instrumentation/instrumentation.gradle
+++ b/dd-java-agent/instrumentation/instrumentation.gradle
@@ -89,6 +89,3 @@ shadowJar {
   }
 }
 
-jar {
-  classifier = 'unbundled'
-}
diff --git a/dd-smoke-tests/cli/cli.gradle b/dd-smoke-tests/cli/cli.gradle
index ebc4e66ede..fedf1fcd4b 100644
--- a/dd-smoke-tests/cli/cli.gradle
+++ b/dd-smoke-tests/cli/cli.gradle
@@ -1,5 +1,5 @@
 plugins {
-  id "com.github.johnrengelman.shadow" version "4.0.4"
+  id "com.github.johnrengelman.shadow" version "5.2.0"
 }
 apply from: "${rootDir}/gradle/java.gradle"
 description = 'Command Line Application Smoke Tests.'
diff --git a/dd-smoke-tests/springboot/springboot.gradle b/dd-smoke-tests/springboot/springboot.gradle
index e6f504cdfe..0804450ed1 100644
--- a/dd-smoke-tests/springboot/springboot.gradle
+++ b/dd-smoke-tests/springboot/springboot.gradle
@@ -1,5 +1,5 @@
 plugins {
-  id "com.github.johnrengelman.shadow" version "4.0.4"
+  id "com.github.johnrengelman.shadow" version "5.2.0"
 }
 apply from: "${rootDir}/gradle/java.gradle"
 description = 'SpringBoot Smoke Tests.'
diff --git a/dd-smoke-tests/wildfly/wildfly.gradle b/dd-smoke-tests/wildfly/wildfly.gradle
index c0c058ef9b..0145bfa3b0 100644
--- a/dd-smoke-tests/wildfly/wildfly.gradle
+++ b/dd-smoke-tests/wildfly/wildfly.gradle
@@ -10,8 +10,11 @@ ext {
 repositories {
   ivy {
     url 'https://download.jboss.org/'
-    layout 'pattern', {
+    patternLayout {
       artifact '/[organisation]/[revision]/[module]/[organisation]-[module]-[revision].[ext]'
+      metadataSources {
+        artifact()
+      }
     }
   }
 }
diff --git a/dd-trace-java.gradle b/dd-trace-java.gradle
index 673bf691a9..0f50c65a26 100644
--- a/dd-trace-java.gradle
+++ b/dd-trace-java.gradle
@@ -1,15 +1,15 @@
 plugins {
   id 'io.franzbecker.gradle-lombok' version '1.14' // Last to support Java 7
-  id 'com.jfrog.artifactory' version '4.8.1'
-  id 'com.jfrog.bintray' version '1.8.4'
-  id 'org.unbroken-dome.test-sets' version '2.1.1'
-  id 'com.github.ben-manes.versions' version '0.21.0'
 
-  id 'com.gradle.build-scan' version '2.2.1'
+  id 'com.jfrog.artifactory' version '4.10.0'
+  id 'com.jfrog.bintray' version '1.8.4'
+  id 'org.unbroken-dome.test-sets' version '2.2.1'
+  id 'com.github.ben-manes.versions' version '0.27.0'
+
   // Not applying google java format by default because it gets confused by stray java build
   // files in 'workspace' build directory in CI
   id 'com.github.sherter.google-java-format' version '0.8' apply false
-  id 'com.dorongold.task-tree' version '1.3.1'
+  id 'com.dorongold.task-tree' version '1.4'
 }
 
 def isCI = System.getenv("CI") != null
@@ -39,18 +39,6 @@ tasks.register("latestDepTest")
 // Applied here to allow publishing of artifactory build info
 apply from: "${rootDir}/gradle/publish.gradle"
 
-def skipBuildscan = Boolean.valueOf(System.getenv("SKIP_BUILDSCAN"))
-
-buildScan {
-  termsOfServiceUrl = 'https://gradle.com/terms-of-service'
-  termsOfServiceAgree = 'yes'
-
-  if (isCI && !skipBuildscan) {
-    publishAlways()
-    tag 'CI'
-  }
-}
-
 wrapper {
   distributionType = Wrapper.DistributionType.ALL
 }
diff --git a/dd-trace-ot/dd-trace-ot.gradle b/dd-trace-ot/dd-trace-ot.gradle
index f6e8e021a6..f943f74e64 100644
--- a/dd-trace-ot/dd-trace-ot.gradle
+++ b/dd-trace-ot/dd-trace-ot.gradle
@@ -1,5 +1,5 @@
 plugins {
-  id "me.champeau.gradle.jmh" version "0.5.0-rc-2"
+  id "me.champeau.gradle.jmh" version "0.5.0"
 }
 
 description = 'dd-trace-ot'
diff --git a/gradle/jacoco.gradle b/gradle/jacoco.gradle
index b77294005a..389627c38c 100644
--- a/gradle/jacoco.gradle
+++ b/gradle/jacoco.gradle
@@ -1,7 +1,7 @@
 apply plugin: "jacoco"
 
 jacoco {
-  toolVersion = "0.8.4"
+  toolVersion = "0.8.5"
 }
 
 jacocoTestReport {
diff --git a/gradle/wrapper/gradle-wrapper.jar b/gradle/wrapper/gradle-wrapper.jar
index 5c2d1cf016..cc4fdc293d 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 3a54a3332e..562e2c8841 100644
--- a/gradle/wrapper/gradle-wrapper.properties
+++ b/gradle/wrapper/gradle-wrapper.properties
@@ -1,5 +1,5 @@
 distributionBase=GRADLE_USER_HOME
 distributionPath=wrapper/dists
-distributionUrl=https\://services.gradle.org/distributions/gradle-5.6.3-all.zip
+distributionUrl=https\://services.gradle.org/distributions/gradle-6.0-all.zip
 zipStoreBase=GRADLE_USER_HOME
 zipStorePath=wrapper/dists
diff --git a/gradlew b/gradlew
index 83f2acfdc3..2fe81a7d95 100755
--- a/gradlew
+++ b/gradlew
@@ -154,19 +154,19 @@ if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
         else
             eval `echo args$i`="\"$arg\""
         fi
-        i=$((i+1))
+        i=`expr $i + 1`
     done
     case $i in
-        (0) set -- ;;
-        (1) set -- "$args0" ;;
-        (2) set -- "$args0" "$args1" ;;
-        (3) set -- "$args0" "$args1" "$args2" ;;
-        (4) set -- "$args0" "$args1" "$args2" "$args3" ;;
-        (5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
-        (6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
-        (7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
-        (8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
-        (9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
     esac
 fi
 
@@ -175,14 +175,9 @@ save () {
     for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
     echo " "
 }
-APP_ARGS=$(save "$@")
+APP_ARGS=`save "$@"`
 
 # Collect all arguments for the java command, following the shell quoting and substitution rules
 eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
 
-# by default we should be in the correct project dir, but when run from Finder on Mac, the cwd is wrong
-if [ "$(uname)" = "Darwin" ] && [ "$HOME" = "$PWD" ]; then
-  cd "$(dirname "$0")"
-fi
-
 exec "$JAVACMD" "$@"
diff --git a/settings.gradle b/settings.gradle
index df7aa8e6a4..4697a62871 100644
--- a/settings.gradle
+++ b/settings.gradle
@@ -1,3 +1,21 @@
+plugins {
+  id 'com.gradle.enterprise' version '3.0'
+}
+
+def isCI = System.getenv("CI") != null
+def skipBuildscan = Boolean.valueOf(System.getenv("SKIP_BUILDSCAN"))
+gradleEnterprise {
+  buildScan {
+    termsOfServiceUrl = 'https://gradle.com/terms-of-service'
+    termsOfServiceAgree = 'yes'
+
+    if (isCI && !skipBuildscan) {
+      publishAlways()
+      tag 'CI'
+    }
+  }
+}
+
 rootProject.name = 'dd-trace-java'
 
 // external apis