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 precedence 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, there are those that 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 resolutions. 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.

  • Sets a proactive security tone for the rest of the year
  • Allows for seamless integration of security goals with new business strategies
  • May coincide with annual compliance reviews and audits, often requiring the attention of multiple departments, which could limit a team’s availability or focus
  • 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.

  • Provides a valuable checkpoint to review and adjust your security posture
  • Helps identify vulnerabilities that may have emerged during the first half of the year
  • Might occur during a busy sales period or when key development projects are underway
  • Can interrupt the rhythm of mid-year internal meetings and strategy evaluations

Reflecting and Preparing at Year’s End

As the year winds down, it is the perfect chance to reflect on the past and plan for the future. You can take this time to perform a comprehensive review of your security posture, taking note of the lessons learned, and prepare to step into the new year with strategies to better fortify your cyber defenses.

  • Offers a thorough review, encouraging reflection and proactive planning
  • Utilizes a generally quieter time to focus on security, allowing for a concentrated effort on building robust defense strategies for the upcoming year
  • May be challenging to gather the necessary teams for collaborative efforts during the test due to vacations and holidays
  • Security firms are often scheduled out months in advance, making it difficult to secure a slot for penetration testing if not planned ahead

Keeping Pace with Technological Shifts

Sometimes, choosing the best time to perform a pen test has nothing to do with the calendar. In some instances, it may be better to schedule it around your business goals and strategies, especially if they include implementing new software or technology to your network infrastructure. By planning your test around these changes, you can make sure you didn’t inadvertently introduce new vulnerabilities.


  • An opportunity to reevaluate strategies in line with the new technological landscape
  • Might cause technical disruptions, especially during the integration of new systems or technologies, requiring focused attention to maintain business continuity
  • Could conflict with ongoing technical assessments or clash with the timeline of other planned implementations, creating a bottleneck in progress and potential delays

Crafting Your Perfect Timeline

Truth be told, the “perfect” time is somewhat of a myth. It’s more about tuning into the rhythm of your organization, understanding its unique pulse, and scheduling these essential ‘health checks’ accordingly. You might find a sweet spot with a full-scale penetration test once a year coupled with quarterly vulnerability scans to maintain a robust security posture.

So, grab your planner and pencil in your penetration test. Because in the grand scheme of things, what truly matters is ensuring it’s a non-negotiable date on your calendar, promising a safer, securer tomorrow.