diff --git a/backend/src/v2/metadata/client.go b/backend/src/v2/metadata/client.go
index cf745d1f3ae..cfd1c2fc0e1 100644
--- a/backend/src/v2/metadata/client.go
+++ b/backend/src/v2/metadata/client.go
@@ -1129,47 +1129,85 @@ func (c *Client) getContextTypeID(ctx context.Context, contextType *pb.ContextTy
 }
 
 func (c *Client) getOrInsertContext(ctx context.Context, name string, contextType *pb.ContextType, customProps map[string]*pb.Value) (*pb.Context, error) {
-	// The most common case -- the context is already created by upstream tasks.
-	// So we try to get the context first.
-	getCtxRes, err := c.svc.GetContextByTypeAndName(ctx, &pb.GetContextByTypeAndNameRequest{TypeName: contextType.Name, ContextName: proto.String(name)})
+	fmt.Printf("getOrInsertContext: name=%q, type=%q\n", name, contextType.GetName())
 
-	if err != nil {
-		return nil, fmt.Errorf("Failed GetContextByTypeAndName(type=%q, name=%q)", contextType.GetName(), name)
-	}
-	// Bug in MLMD GetContextsByTypeAndName? It doesn't return error even when no
-	// context was found.
-	if getCtxRes.Context != nil {
-		return getCtxRes.Context, nil
-	}
+	// This function is known to be flaky and racy right after a server is initially created
+	// and pipeline runs are just starting, so we retry up to 3 times. The actual cause of the
+	// race isn't fully understood, but it's probably caused by deadlocks in MLMD SQL code.
+	// General MySQL advice is to retry on deadlock errors, so here we are.
 
-	// Get the ContextType ID.
-	typeID, err := c.getContextTypeID(ctx, contextType)
-	if err != nil {
-		return nil, err
-	}
-	// Next, create the Context.
-	putReq := &pb.PutContextsRequest{
-		Contexts: []*pb.Context{
-			{
-				Name:             proto.String(name),
-				TypeId:           proto.Int64(typeID),
-				CustomProperties: customProps,
+	for i := 1; i <= 3; i++ {
+
+		fmt.Printf("getOrInsertContext: attempt %v\n", i)
+		// The most common case -- the context is already created by previous tasks.
+		// So we try to get the context first.
+
+		fmt.Printf("getOrInsertContext: calling GetContextByTypeAndName\n")
+
+		getCtxRes, err := c.svc.GetContextByTypeAndName(ctx, &pb.GetContextByTypeAndNameRequest{TypeName: contextType.Name, ContextName: proto.String(name)})
+		fmt.Printf("getOrInsertContext: response=%v, err=%v\n", getCtxRes, err)
+
+		// grpc returns a nil response if there was an error
+		if err != nil {
+			fmt.Printf("getOrInsertContext: error=%v\n", err)
+			fmt.Println(fmt.Errorf("failed GetContextByTypeAndName(type=%q, name=%q), error=%w", contextType.GetName(), name, err))
+			time.Sleep(1 * time.Second)
+			continue
+		}
+
+		if getCtxRes.Context != nil {
+			fmt.Printf("getOrInsertContext: context found: %v\n", getCtxRes.Context)
+			return getCtxRes.Context, nil
+		}
+
+		fmt.Printf("getOrInsertContext: context not found, creating\n")
+
+		// Get the ContextType ID.
+		typeID, err := c.getContextTypeID(ctx, contextType)
+		if err != nil {
+			fmt.Printf("getOrInsertContext: error getting getContextTypeID for creation: %v\n", err)
+			time.Sleep(1 * time.Second)
+			continue
+		}
+		// Next, create the Context.
+		putReq := &pb.PutContextsRequest{
+			Contexts: []*pb.Context{
+				{
+					Name:             proto.String(name),
+					TypeId:           proto.Int64(typeID),
+					CustomProperties: customProps,
+				},
 			},
-		},
-	}
-	_, err = c.svc.PutContexts(ctx, putReq)
-	// It's expected other tasks may try to create the context at the same time,
-	// so ignore AlreadyExists error.
-	if err != nil && status.Convert(err).Code() != codes.AlreadyExists {
-		return nil, fmt.Errorf("Failed PutContext(name=%q, type=%q, typeid=%v): %w", name, contextType.GetName(), typeID, err)
-	}
+		}
+		fmt.Printf("getOrInsertContext: sending create request\n")
+		_, err = c.svc.PutContexts(ctx, putReq)
+		// It's expected other tasks may try to create the context at the same time,
+		// so ignore AlreadyExists error.
+		if err != nil {
+			if status.Convert(err).Code() != codes.AlreadyExists {
+				fmt.Println(fmt.Errorf("failed PutContext(name=%q, type=%q, typeid=%v): %w", name, contextType.GetName(), typeID, err))
+				time.Sleep(1 * time.Second)
+				continue
+			} else {
+				fmt.Printf("getOrInsertContext: context now already exists, someone beat us to it\n")
+			}
+		} else {
+			fmt.Printf("getOrInsertContext: context created successfully\n")
+		}
 
-	// Get the created context.
-	getCtxRes, err = c.svc.GetContextByTypeAndName(ctx, &pb.GetContextByTypeAndNameRequest{TypeName: contextType.Name, ContextName: proto.String(name)})
-	if err != nil {
-		return nil, fmt.Errorf("Failed GetContext(name=%q, type=%q): %w", name, contextType.GetName(), err)
+		// Get the created context.
+		fmt.Printf("getOrInsertContext: now getting the context we just created\n")
+		getCtxRes, err = c.svc.GetContextByTypeAndName(ctx, &pb.GetContextByTypeAndNameRequest{TypeName: contextType.Name, ContextName: proto.String(name)})
+		if err != nil {
+			fmt.Println(fmt.Errorf("failed GetContext(name=%q, type=%q): %w", name, contextType.GetName(), err))
+			time.Sleep(1 * time.Second)
+			continue
+		}
+		fmt.Printf("getOrInsertContext: successfully got context, returning it :)\n")
+		return getCtxRes.GetContext(), nil
 	}
-	return getCtxRes.GetContext(), nil
+
+	return nil, fmt.Errorf("failed to get or insert context %q after 3 attempts", name)
 }
 
 func GenerateExecutionConfig(executorInput *pipelinespec.ExecutorInput) (*ExecutionConfig, error) {