I would not say that there are times when outsourcing is a bad idea. There are, however, pieces of information of which you should be aware before you decide to outsource. You should consider your customer base, their needs, and your daily operations. If your customers often have complex situations that vary widely from one customer to another, that typically means that anyone working for your company must have in-depth knowledge about your organization and all needs that may arise. This may mean that a case by case contract for your outsourced company may not work. You may need more hands-on attention from your outsourced company. This is not a problem that should prevent you from outsourcing, just a situation you should consider. Before you contact a company like Arctic It, consider these points. 

Some other points to consider is that when you outsource, you may not be able to quality control the service that is provided from your outsourced company. It will be a third party company, and they will not have all the knowledge that an in-house employee has. You cannot control the employees of the third party company. You cannot control who is hired and how they are trained. You have to have some amount of faith in the company you hire. This is a business the same as yours, and they work hard to hire professionals that are well trained and knowledgeable at their jobs. 

You may find that you do not have as much direct contact with some of your employees or customers. When you have outsourced technical support, they often act as a middle man between you and your customers. This may cause you to feel out of touch with your customers. If you have a third party interacting with your customers, they may only be able to handle a standard set of problems. They usually have a prescribed method of handling problems, and when something falls outside of that, they may not be able to assist your customer properly. If you do not have a system for tracking these specific customers, they may get lost in the shuffle. This could lead to poor customer service and even lost customers. You want to make sure you have a system to capture this specific situation, so it does not lead to lost revenue.

These are potential challenges of which you should be aware. They are not insurmountable, but you do have to be aware of them. When you are aware of them, you can put plans in place to mitigate them and address them before they become real problems.