diff --git a/src/adservice/Dockerfile b/src/adservice/Dockerfile
index 86c2864eb4..26b3288cc1 100644
--- a/src/adservice/Dockerfile
+++ b/src/adservice/Dockerfile
@@ -29,7 +29,8 @@ ARG version=1.19.1
 WORKDIR /usr/src/app/
 
 COPY --from=builder /usr/src/app/ ./
-ADD https://github.com/open-telemetry/opentelemetry-java-instrumentation/releases/download/v$version/opentelemetry-javaagent.jar /app/opentelemetry-javaagent.jar
+ADD https://search.maven.org/remotecontent?filepath=io/sentry/sentry-opentelemetry-agent/6.9.2/sentry-opentelemetry-agent-6.9.2.jar /app/opentelemetry-javaagent.jar
+
 ENV JAVA_TOOL_OPTIONS=-javaagent:/app/opentelemetry-javaagent.jar
 
 EXPOSE ${AD_SERVICE_PORT}
diff --git a/src/adservice/build.gradle b/src/adservice/build.gradle
index 40bc08af59..0a43f693a5 100644
--- a/src/adservice/build.gradle
+++ b/src/adservice/build.gradle
@@ -14,8 +14,8 @@ description = 'Ad Service'
 group = "adservice"
 version = "0.1.0-SNAPSHOT"
 
-def opentelemetryVersion = "1.19.0"
-def opentelemetryInstrumentationAlphaVersion = "1.19.1-alpha"
+def opentelemetryVersion = "1.20.1"
+def opentelemetryInstrumentationAlphaVersion = "1.20.2-alpha"
 def grpcVersion = "1.45.1"
 def jacksonVersion = "2.13.2"
 def protocVersion = "3.20.0"
@@ -46,7 +46,9 @@ dependencies {
                 "io.opentelemetry:opentelemetry-api",
                 "io.opentelemetry:opentelemetry-sdk",
                 "io.opentelemetry.instrumentation:opentelemetry-instrumentation-annotations",
-                "org.apache.logging.log4j:log4j-core:2.17.2"
+                "org.apache.logging.log4j:log4j-core:2.17.2",
+                "io.sentry:sentry:6.9.2",
+                "io.sentry:sentry-opentelemetry-core:6.9.2"
 
         runtimeOnly "com.fasterxml.jackson.core:jackson-core:${jacksonVersion}",
                 "com.fasterxml.jackson.core:jackson-databind:${jacksonVersion}",
diff --git a/src/adservice/src/main/java/hipstershop/AdService.java b/src/adservice/src/main/java/hipstershop/AdService.java
index a09ed9e580..602140a931 100644
--- a/src/adservice/src/main/java/hipstershop/AdService.java
+++ b/src/adservice/src/main/java/hipstershop/AdService.java
@@ -41,6 +41,10 @@
 import java.util.Collection;
 import java.util.List;
 import java.util.Random;
+
+import io.sentry.Instrumenter;
+import io.sentry.opentelemetry.OpenTelemetryLinkErrorEventProcessor;
+import io.sentry.Sentry;
 import org.apache.logging.log4j.Level;
 import org.apache.logging.log4j.LogManager;
 import org.apache.logging.log4j.Logger;
@@ -131,6 +135,14 @@ public void getAds(AdRequest req, StreamObserver<AdResponse> responseObserver) {
         span.setStatus(StatusCode.ERROR);
         logger.log(Level.WARN, "GetAds Failed with status {}", e.getStatus());
         responseObserver.onError(e);
+        Sentry.captureException(e);
+      } catch (IllegalArgumentException e) {
+        span.addEvent(
+                "Error", Attributes.of(AttributeKey.stringKey("exception.message"), e.getMessage()));
+        span.setStatus(StatusCode.ERROR);
+        logger.log(Level.WARN, "GetAds Failed with message {}", e.getMessage());
+        Sentry.captureException(e);
+        responseObserver.onError(e);
       }
     }
   }
@@ -139,6 +151,9 @@ public void getAds(AdRequest req, StreamObserver<AdResponse> responseObserver) {
 
   @WithSpan("getAdsByCategory")
   private Collection<Ad> getAdsByCategory(@SpanAttribute("app.ads.category") String category) {
+    if ("telescopes".equals(category)) {
+      throw new IllegalArgumentException("Thrown on purpose for category " + category);
+    }
     Collection<Ad> ads = adsMap.get(category);
     Span.current().setAttribute("app.ads.count", ads.size());
     return ads;
@@ -229,6 +244,23 @@ private static ImmutableListMultimap<String, Ad> createAdsMap() {
 
   /** Main launches the server from the command line. */
   public static void main(String[] args) throws IOException, InterruptedException {
+    logger.info("Initializing Sentry");
+    Sentry.init(options -> {
+      // NOTE: SENTRY_DSN is injected as environment variable and this config setting picks it up
+      options.setEnableExternalConfiguration(true);
+
+      // This is required for the Sentry Java Agent to actually perform instrumentation
+      options.setInstrumenter(Instrumenter.OTEL);
+
+      options.addEventProcessor(new OpenTelemetryLinkErrorEventProcessor());
+
+      // Send all transactions to Sentry
+      options.setTracesSampleRate(1.0);
+
+      // Enable this to see more logs
+      // options.setDebug(true);
+    });
+
     // Start the RPC server. You shouldn't see any output from gRPC before this.
     logger.info("AdService starting.");
     final AdService service = AdService.getInstance();