diff --git a/dd-java-agent-ittests/src/test/groovy/datadog/trace/agent/integration/httpclient/ApacheHttpClientTest.groovy b/dd-java-agent-ittests/src/test/groovy/datadog/trace/agent/integration/httpclient/ApacheHttpClientTest.groovy
index 0aca749caa..d378079ad8 100644
--- a/dd-java-agent-ittests/src/test/groovy/datadog/trace/agent/integration/httpclient/ApacheHttpClientTest.groovy
+++ b/dd-java-agent-ittests/src/test/groovy/datadog/trace/agent/integration/httpclient/ApacheHttpClientTest.groovy
@@ -64,7 +64,7 @@ class ApacheHttpClientTest extends Specification {
     final DDSpan localSpan = clientTrace.get(1)
     localSpan.getType() == null
     localSpan.getTags()[Tags.COMPONENT.getKey()] == "apache-httpclient"
-    localSpan.getOperationName() == "http.request"
+    localSpan.getOperationName() == "apache.http"
 
     final DDSpan clientSpan = clientTrace.get(2)
     clientSpan.getOperationName() == "http.request"
@@ -109,7 +109,7 @@ class ApacheHttpClientTest extends Specification {
     // our instrumentation makes 2 spans for apache-httpclient
     final DDSpan localSpan = clientTrace.get(1)
     localSpan.getTags()[Tags.COMPONENT.getKey()] == "apache-httpclient"
-    localSpan.getOperationName() == "http.request"
+    localSpan.getOperationName() == "apache.http"
 
     final DDSpan clientSpan = clientTrace.get(2)
     clientSpan.getOperationName() == "http.request"
diff --git a/dd-java-agent/instrumentation/aws-sdk/src/test/groovy/AWSClientTest.groovy b/dd-java-agent/instrumentation/aws-sdk/src/test/groovy/AWSClientTest.groovy
index 7c557c85df..1303c148ad 100644
--- a/dd-java-agent/instrumentation/aws-sdk/src/test/groovy/AWSClientTest.groovy
+++ b/dd-java-agent/instrumentation/aws-sdk/src/test/groovy/AWSClientTest.groovy
@@ -100,9 +100,9 @@ class AWSClientTest extends AgentTestRunner {
     and: // span 0 - from apache-httpclient instrumentation
     def span1 = trace[0]
 
-    span1.context().operationName == "http.request"
+    span1.context().operationName == "apache.http"
     span1.serviceName == "unnamed-java-app"
-    span1.resourceName == "http.request"
+    span1.resourceName == "apache.http"
     span1.type == null
     !span1.context().getErrorFlag()
     span1.context().parentId == 0
diff --git a/dd-java-agent/instrumentation/jax-rs-client/src/test/groovy/JaxRsClientTest.groovy b/dd-java-agent/instrumentation/jax-rs-client/src/test/groovy/JaxRsClientTest.groovy
index 35638b88e6..5ffae43521 100644
--- a/dd-java-agent/instrumentation/jax-rs-client/src/test/groovy/JaxRsClientTest.groovy
+++ b/dd-java-agent/instrumentation/jax-rs-client/src/test/groovy/JaxRsClientTest.groovy
@@ -58,7 +58,7 @@ class JaxRsClientTest extends AgentTestRunner {
 
     span.context().operationName == "jax-rs.client.call"
     span.serviceName == "unnamed-java-app"
-    span.resourceName == "GET jax-rs.client.call"
+    span.resourceName == "GET /ping"
     span.type == "http"
     !span.context().getErrorFlag()
     span.context().parentId == 0
diff --git a/dd-java-agent/instrumentation/okhttp-3/src/test/groovy/OkHttp3Test.groovy b/dd-java-agent/instrumentation/okhttp-3/src/test/groovy/OkHttp3Test.groovy
index 3529277cd4..10866979e6 100644
--- a/dd-java-agent/instrumentation/okhttp-3/src/test/groovy/OkHttp3Test.groovy
+++ b/dd-java-agent/instrumentation/okhttp-3/src/test/groovy/OkHttp3Test.groovy
@@ -1,4 +1,5 @@
 import datadog.trace.agent.test.AgentTestRunner
+import datadog.trace.api.DDSpanTypes
 import datadog.trace.api.DDTags
 import io.opentracing.tag.Tags
 import okhttp3.OkHttpClient
@@ -39,19 +40,20 @@ class OkHttp3Test extends AgentTestRunner {
     and: // span 0
     def span1 = trace[0]
 
-    span1.context().operationName == "http.request"
-    span1.serviceName == "unnamed-java-app"
-    span1.resourceName == "http.request"
-    span1.type == null
+    span1.context().operationName == "okhttp.http"
+    span1.serviceName == "okhttp"
+    span1.resourceName == "okhttp.http"
+    span1.type == DDSpanTypes.WEB_SERVLET
     !span1.context().getErrorFlag()
     span1.context().parentId == 0
 
 
     def tags1 = span1.context().tags
     tags1["component"] == "okhttp"
+    tags1["span.type"] == DDSpanTypes.WEB_SERVLET
     tags1["thread.name"] != null
     tags1["thread.id"] != null
-    tags1.size() == 3
+    tags1.size() == 4
 
     and: // span 1
     def span2 = trace[1]
diff --git a/dd-java-agent/instrumentation/servlet-2/src/test/groovy/JettyServlet2Test.groovy b/dd-java-agent/instrumentation/servlet-2/src/test/groovy/JettyServlet2Test.groovy
index 2d36fb3416..53fc9fab2f 100644
--- a/dd-java-agent/instrumentation/servlet-2/src/test/groovy/JettyServlet2Test.groovy
+++ b/dd-java-agent/instrumentation/servlet-2/src/test/groovy/JettyServlet2Test.groovy
@@ -106,6 +106,7 @@ class JettyServlet2Test extends AgentTestRunner {
             "span.kind" "server"
             "component" "java-web-servlet"
             "span.type" DDSpanTypes.WEB_SERVLET
+            "servlet.context" ""
             defaultTags()
           }
         }
@@ -143,6 +144,7 @@ class JettyServlet2Test extends AgentTestRunner {
             "span.kind" "server"
             "component" "java-web-servlet"
             "span.type" DDSpanTypes.WEB_SERVLET
+            "servlet.context" ""
             errorTags(RuntimeException, "some $path error")
             defaultTags()
           }
@@ -182,6 +184,7 @@ class JettyServlet2Test extends AgentTestRunner {
             "span.kind" "server"
             "component" "java-web-servlet"
             "span.type" DDSpanTypes.WEB_SERVLET
+            "servlet.context" ""
             defaultTags()
           }
         }
diff --git a/dd-java-agent/instrumentation/servlet-3/src/test/groovy/JettyServlet3Test.groovy b/dd-java-agent/instrumentation/servlet-3/src/test/groovy/JettyServlet3Test.groovy
index bdd3258a8c..a581a229c6 100644
--- a/dd-java-agent/instrumentation/servlet-3/src/test/groovy/JettyServlet3Test.groovy
+++ b/dd-java-agent/instrumentation/servlet-3/src/test/groovy/JettyServlet3Test.groovy
@@ -108,6 +108,7 @@ class JettyServlet3Test extends AgentTestRunner {
             "span.kind" "server"
             "component" "java-web-servlet"
             "span.type" DDSpanTypes.WEB_SERVLET
+            "servlet.context" ""
             "http.status_code" 200
             defaultTags()
           }
@@ -147,6 +148,7 @@ class JettyServlet3Test extends AgentTestRunner {
             "span.kind" "server"
             "component" "java-web-servlet"
             "span.type" DDSpanTypes.WEB_SERVLET
+            "servlet.context" ""
             "http.status_code" 500
             errorTags(RuntimeException, "some $path error")
             defaultTags()
@@ -187,6 +189,7 @@ class JettyServlet3Test extends AgentTestRunner {
             "span.kind" "server"
             "component" "java-web-servlet"
             "span.type" DDSpanTypes.WEB_SERVLET
+            "servlet.context" ""
             "http.status_code" 500
             "error" true
             defaultTags()
diff --git a/dd-java-agent/instrumentation/spring-web/src/test/groovy/test/SpringBootBasedTest.groovy b/dd-java-agent/instrumentation/spring-web/src/test/groovy/test/SpringBootBasedTest.groovy
index 1a3e424c88..bf1132d667 100644
--- a/dd-java-agent/instrumentation/spring-web/src/test/groovy/test/SpringBootBasedTest.groovy
+++ b/dd-java-agent/instrumentation/spring-web/src/test/groovy/test/SpringBootBasedTest.groovy
@@ -49,10 +49,11 @@ class SpringBootBasedTest extends AgentTestRunner {
     span.context().tags["span.kind"] == "server"
     span.context().tags["span.type"] == "web"
     span.context().tags["component"] == "java-web-servlet"
+    span.context().tags["servlet.context"] == ""
     span.context().tags["http.status_code"] == 200
     span.context().tags["thread.name"] != null
     span.context().tags["thread.id"] != null
-    span.context().tags.size() == 8
+    span.context().tags.size() == 9
   }
 
   def "generates 404 spans"() {
@@ -78,10 +79,11 @@ class SpringBootBasedTest extends AgentTestRunner {
     span0.context().tags["span.kind"] == "server"
     span0.context().tags["span.type"] == "web"
     span0.context().tags["component"] == "java-web-servlet"
+    span0.context().tags["servlet.context"] == ""
     span0.context().tags["http.status_code"] == 404
     span0.context().tags["thread.name"] != null
     span0.context().tags["thread.id"] != null
-    span0.context().tags.size() == 8
+    span0.context().tags.size() == 9
 
     and: // trace 1
     def trace1 = TEST_WRITER.get(1)
@@ -98,10 +100,11 @@ class SpringBootBasedTest extends AgentTestRunner {
     span1.context().tags["span.kind"] == "server"
     span1.context().tags["span.type"] == "web"
     span1.context().tags["component"] == "java-web-servlet"
+    span1.context().tags["servlet.context"] == ""
     span1.context().tags["http.status_code"] == 404
     span1.context().tags["thread.name"] != null
     span1.context().tags["thread.id"] != null
-    span1.context().tags.size() == 8
+    span1.context().tags.size() == 9
   }
 
   def "generates error spans"() {
@@ -129,6 +132,7 @@ class SpringBootBasedTest extends AgentTestRunner {
     span0.context().tags["span.kind"] == "server"
     span0.context().tags["span.type"] == "web"
     span0.context().tags["component"] == "java-web-servlet"
+    span0.context().tags["servlet.context"] == ""
     span0.context().tags["http.status_code"] == 500
     span0.context().tags["thread.name"] != null
     span0.context().tags["thread.id"] != null
@@ -136,7 +140,7 @@ class SpringBootBasedTest extends AgentTestRunner {
     span0.context().tags["error.msg"] == "Request processing failed; nested exception is java.lang.RuntimeException: qwerty"
     span0.context().tags["error.type"] == NestedServletException.getName()
     span0.context().tags["error.stack"] != null
-    span0.context().tags.size() == 12
+    span0.context().tags.size() == 13
 
     and: // trace 1
     def trace1 = TEST_WRITER.get(1)
@@ -152,11 +156,12 @@ class SpringBootBasedTest extends AgentTestRunner {
     span1.context().tags["span.kind"] == "server"
     span1.context().tags["span.type"] == "web"
     span1.context().tags["component"] == "java-web-servlet"
+    span1.context().tags["servlet.context"] == ""
     span1.context().tags["http.status_code"] == 500
     span1.context().getErrorFlag()
     span1.context().tags["thread.name"] != null
     span1.context().tags["thread.id"] != null
-    span1.context().tags.size() == 9
+    span1.context().tags.size() == 10
   }
 
   def "validated form"() {
@@ -179,10 +184,11 @@ class SpringBootBasedTest extends AgentTestRunner {
     span.context().tags["span.kind"] == "server"
     span.context().tags["span.type"] == "web"
     span.context().tags["component"] == "java-web-servlet"
+    span.context().tags["servlet.context"] == ""
     span.context().tags["http.status_code"] == 200
     span.context().tags["thread.name"] != null
     span.context().tags["thread.id"] != null
-    span.context().tags.size() == 8
+    span.context().tags.size() == 9
   }
 
   def "invalid form"() {
@@ -210,6 +216,7 @@ class SpringBootBasedTest extends AgentTestRunner {
     span0.context().tags["span.kind"] == "server"
     span0.context().tags["span.type"] == "web"
     span0.context().tags["component"] == "java-web-servlet"
+    span0.context().tags["servlet.context"] == ""
     span0.context().tags["http.status_code"] == 400
     span0.context().tags["thread.name"] != null
     span0.context().tags["thread.id"] != null
@@ -217,7 +224,7 @@ class SpringBootBasedTest extends AgentTestRunner {
     span0.context().tags["error.msg"].toString().startsWith("Validation failed")
     span0.context().tags["error.type"] == MethodArgumentNotValidException.getName()
     span0.context().tags["error.stack"] != null
-    span0.context().tags.size() == 12
+    span0.context().tags.size() == 13
 
     and: // trace 1
     def trace1 = TEST_WRITER.get(1)
@@ -234,9 +241,10 @@ class SpringBootBasedTest extends AgentTestRunner {
     span1.context().tags["span.kind"] == "server"
     span1.context().tags["span.type"] == "web"
     span1.context().tags["component"] == "java-web-servlet"
+    span1.context().tags["servlet.context"] == ""
     span1.context().tags["http.status_code"] == 400
     span1.context().tags["thread.name"] != null
     span1.context().tags["thread.id"] != null
-    span1.context().tags.size() == 8
+    span1.context().tags.size() == 9
   }
 }
diff --git a/dd-java-agent/testing/src/main/groovy/datadog/trace/agent/test/TagsAssert.groovy b/dd-java-agent/testing/src/main/groovy/datadog/trace/agent/test/TagsAssert.groovy
index 3565daae73..8851d5670f 100644
--- a/dd-java-agent/testing/src/main/groovy/datadog/trace/agent/test/TagsAssert.groovy
+++ b/dd-java-agent/testing/src/main/groovy/datadog/trace/agent/test/TagsAssert.groovy
@@ -4,10 +4,10 @@ import datadog.opentracing.DDSpan
 
 class TagsAssert {
   private final Map<String, Object> tags
-  private final Set<String> assertedTags = new HashSet<>()
+  private final Set<String> assertedTags = new TreeSet<>()
 
   private TagsAssert(DDSpan span) {
-    this.tags = span.tags
+    this.tags = new TreeMap(span.tags)
   }
 
   static TagsAssert assertTags(DDSpan span,
diff --git a/dd-trace-ot/src/main/java/datadog/opentracing/DDTracer.java b/dd-trace-ot/src/main/java/datadog/opentracing/DDTracer.java
index 8d19dabdf6..f15feaa92d 100644
--- a/dd-trace-ot/src/main/java/datadog/opentracing/DDTracer.java
+++ b/dd-trace-ot/src/main/java/datadog/opentracing/DDTracer.java
@@ -27,7 +27,6 @@ import java.util.Collection;
 import java.util.Collections;
 import java.util.Comparator;
 import java.util.HashMap;
-import java.util.Iterator;
 import java.util.List;
 import java.util.Map;
 import java.util.Properties;
@@ -517,12 +516,9 @@ public class DDTracer implements io.opentracing.Tracer {
               DDTracer.this);
 
       // Apply Decorators to handle any tags that may have been set via the builder.
-      for (final Iterator<Map.Entry<String, Object>> it = this.tags.entrySet().iterator();
-          it.hasNext();
-          ) {
-        final Map.Entry<String, Object> tag = it.next();
+      for (final Map.Entry<String, Object> tag : this.tags.entrySet()) {
         if (tag.getValue() == null) {
-          it.remove();
+          context.setTag(tag.getKey(), null);
           continue;
         }
 
@@ -545,7 +541,7 @@ public class DDTracer implements io.opentracing.Tracer {
         }
 
         if (!addTag) {
-          it.remove();
+          context.setTag(tag.getKey(), null);
         }
       }