Timing is everything, and if you're anything like me, you live by your task list. Every task must have a deadline or face the possibility of falling through the cracks. When it comes to cybersecurity and compliance, however, that simply isn't an option.
As you're developing your annual cybersecurity strategy and goals, it is important to attach deadlines to your initiatives, such as when to perform your annual pen test. There are several factors to consider when selecting your next deadline.
For some, performing a test right at the beginning of the year helps set a precedent for the following months by starting with a secure foundation. For others, a mid-year check-up gives them a chance to figure out what is working and what needs improvement. Then, some like the end of the year to use those findings when crafting next year's security strategy.
While we can't tell you which is best for your organization, we can highlight the pros and cons of each approach.
Kicking Off the Year on a Secure Note
Imagine hitting the ground running as the new year begins, with a security strategy that's as fresh and ready as your New Year's resolution. An early bird approach to penetration testing can offer just that – a chance to start off with a bang, building a robust security posture from the get-go.
Pros
- Sets a proactive security tone for the rest of the year
- Allows for seamless integration of security goals with new business strategies
Cons
- May coincide with annual compliance reviews and audits, often requiring the attention of multiple departments, which could limit a team’s availability or focus
- It could coincide with budget allocations and planning, making financial resources a bit tight
The Mid-Year Checkpoint
Think of a mid-year penetration test as a checkpoint in a marathon. It's a chance to pause, evaluate, and perhaps change your plans if they need to be adjusted. It gives you the space to tweak your strategies, ensuring you're not just running, but sprinting towards a secure finish line.
Pros
- Provides a valuable checkpoint to review and adjust your security posture


