diff --git a/flyteplugins/go/tasks/plugins/webapi/agent/plugin.go b/flyteplugins/go/tasks/plugins/webapi/agent/plugin.go
index 77a27b6699..4f518ced55 100644
--- a/flyteplugins/go/tasks/plugins/webapi/agent/plugin.go
+++ b/flyteplugins/go/tasks/plugins/webapi/agent/plugin.go
@@ -80,11 +80,11 @@ func (p *Plugin) Create(ctx context.Context, taskCtx webapi.TaskExecutionContext
 	webapi.Resource, error) {
 	taskTemplate, err := taskCtx.TaskReader().Read(ctx)
 	if err != nil {
-		return nil, nil, err
+		return nil, nil, fmt.Errorf("failed to read task template with error: %v", err)
 	}
 	inputs, err := taskCtx.InputReader().Get(ctx)
 	if err != nil {
-		return nil, nil, err
+		return nil, nil, fmt.Errorf("failed to read inputs with error: %v", err)
 	}
 
 	var argTemplate []string
@@ -98,7 +98,7 @@ func (p *Plugin) Create(ctx context.Context, taskCtx webapi.TaskExecutionContext
 		argTemplate = taskTemplate.GetContainer().GetArgs()
 		modifiedArgs, err := template.Render(ctx, taskTemplate.GetContainer().GetArgs(), templateParameters)
 		if err != nil {
-			return nil, nil, err
+			return nil, nil, fmt.Errorf("failed to render args with error: %v", err)
 		}
 		taskTemplate.GetContainer().Args = modifiedArgs
 		defer func() {
@@ -135,7 +135,7 @@ func (p *Plugin) Create(ctx context.Context, taskCtx webapi.TaskExecutionContext
 	request := &admin.CreateTaskRequest{Inputs: inputs, Template: taskTemplate, OutputPrefix: outputPrefix, TaskExecutionMetadata: &taskExecutionMetadata}
 	res, err := client.CreateTask(finalCtx, request)
 	if err != nil {
-		return nil, nil, err
+		return nil, nil, fmt.Errorf("failed to create task from agent with %v", err)
 	}
 
 	return ResourceMetaWrapper{
@@ -153,7 +153,8 @@ func (p *Plugin) ExecuteTaskSync(
 ) (webapi.ResourceMeta, webapi.Resource, error) {
 	stream, err := client.ExecuteTaskSync(ctx)
 	if err != nil {
-		return nil, nil, err
+		logger.Errorf(ctx, "failed to execute task from agent with %v", err)
+		return nil, nil, fmt.Errorf("failed to execute task from agent with %v", err)
 	}
 
 	headerProto := &admin.ExecuteTaskSyncRequest{
@@ -185,8 +186,8 @@ func (p *Plugin) ExecuteTaskSync(
 
 	in, err := stream.Recv()
 	if err != nil {
-		logger.Errorf(ctx, "failed to receive from server %s", err.Error())
-		return nil, nil, err
+		logger.Errorf(ctx, "failed to receive stream from server %s", err.Error())
+		return nil, nil, fmt.Errorf("failed to receive stream from server %w", err)
 	}
 	if in.GetHeader() == nil {
 		return nil, nil, fmt.Errorf("expected header in the response, but got none")
@@ -202,7 +203,7 @@ func (p *Plugin) ExecuteTaskSync(
 		LogLinks:   resource.GetLogLinks(),
 		CustomInfo: resource.GetCustomInfo(),
 		AgentError: resource.GetAgentError(),
-	}, err
+	}, nil
 }
 
 func (p *Plugin) Get(ctx context.Context, taskCtx webapi.GetContext) (latest webapi.Resource, err error) {
@@ -223,7 +224,7 @@ func (p *Plugin) Get(ctx context.Context, taskCtx webapi.GetContext) (latest web
 	}
 	res, err := client.GetTask(finalCtx, request)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to get task from agent with %v", err)
 	}
 
 	return ResourceWrapper{
@@ -256,7 +257,7 @@ func (p *Plugin) Delete(ctx context.Context, taskCtx webapi.DeleteContext) error
 		ResourceMeta: metadata.AgentResourceMeta,
 	}
 	_, err = client.DeleteTask(finalCtx, request)
-	return err
+	return fmt.Errorf("failed to delete task from agent with %v", err)
 }
 
 func (p *Plugin) Status(ctx context.Context, taskCtx webapi.StatusContext) (phase core.PhaseInfo, err error) {
@@ -307,7 +308,7 @@ func (p *Plugin) Status(ctx context.Context, taskCtx webapi.StatusContext) (phas
 		err = writeOutput(ctx, taskCtx, resource.Outputs)
 		if err != nil {
 			logger.Errorf(ctx, "failed to write output with err %s", err.Error())
-			return core.PhaseInfoUndefined, err
+			return core.PhaseInfoUndefined, fmt.Errorf("failed to write output with err %s", err.Error())
 		}
 		return core.PhaseInfoSuccess(taskInfo), nil
 	}