diff --git a/packages/datadog-instrumentations/src/http2/client.js b/packages/datadog-instrumentations/src/http2/client.js
index d91cea4e1d5..e5a3cd9f4ad 100644
--- a/packages/datadog-instrumentations/src/http2/client.js
+++ b/packages/datadog-instrumentations/src/http2/client.js
@@ -33,11 +33,11 @@ function createWrapRequest (authority, options) {
       const ctx = { headers, authority, options }
 
       return startChannel.runStores(ctx, () => {
-        const req = request.apply(this, arguments)
+        try {
+          const req = request.apply(this, arguments)
 
-        shimmer.wrap(req, 'emit', createWrapEmit(ctx))
+          shimmer.wrap(req, 'emit', createWrapEmit(ctx))
 
-        try {
           return req
         } catch (e) {
           ctx.error = e
diff --git a/packages/dd-trace/src/plugins/tracing.js b/packages/dd-trace/src/plugins/tracing.js
index e585b1290d0..5ccdedb1e4f 100644
--- a/packages/dd-trace/src/plugins/tracing.js
+++ b/packages/dd-trace/src/plugins/tracing.js
@@ -84,6 +84,8 @@ class TracingPlugin extends Plugin {
     const span = this.activeSpan
 
     if (!span._spanContext._tags['error']) {
+      // Errors may be wrapped in a context.
+      error = (error && error.error) || error
       span.setTag('error', error || 1)
     }
   }