šŸ¤•IPsec | The Networking Pain That Makes You Question Your Life ChoicesšŸ¤®

Ronald BartelsRonald Bartels
4 min read

If you've ever troubleshot an IPsec VPN, you know the painā€¦

šŸ”§ Hours of tweaking settings
šŸ” Digging through logs
šŸ“ Double-checking configs

Is it the pre-shared key?
The phase 1 settings?
Or the VPN gods testing you again?

And after hours of frustration, you discover the issue was something utterly stupidā€”
like a mismatched phase setting, a forgotten NAT rule, or the firewall silently dropping traffic for reasons known only to the spirits of the underworld.

IPsec is the kind of technology that turns experienced network engineers into broken, caffeine-dependent shells of their former selves. Itā€™s equal parts technical challenge and existential crisis.

You start by questioning your configs.
Then you question your equipment.
Eventually, you question your entire career path.

But hey, at least youā€™ll never forget that subnet mask again, right?

Letā€™s talk about why IPsec is the worst thing to ever happen to networkingā€”and why the solution to reclaiming your sanity is to embrace SD-WAN.


What is IPsec, & Why is it a Nightmare?

IPsec (Internet Protocol Security) was designed to create secure tunnels between networks over the internet. Sounds great, right? The problem is everything else about it.

IPsec consists of two main phases:
1ļøāƒ£ Phase 1 (IKE) ā€“ Where the two devices establish a secure connection.
2ļøāƒ£ Phase 2 (ESP) ā€“ Where the actual encrypted traffic flows.

In theory, itā€™s simple. In practice, itā€™s a horror show.

Why IPsec is a Living Nightmare

šŸ’€ 1. Too Many Moving Parts

  • Youā€™ve got pre-shared keys, encryption algorithms, hash functions, lifetimes, and modes to align perfectly on both sides.

  • One tiny mismatch and nothing worksā€”with no helpful error messages to guide you.

šŸ’€ 2. Debugging is a Torture Method

  • Error messages like ā€œNO_PROPOSAL_CHOSENā€ are cryptic at best.

  • Vendor logs give you more hexadecimal than actual human-readable explanations.

  • Often, youā€™re left guessing which setting is wrongā€”because IPsec wonā€™t tell you outright.

šŸ’€ 3. NAT is IPsecā€™s Mortal Enemy

  • If your traffic goes through NAT, IPsec often just stops working.

  • Special NAT Traversal (NAT-T) modes are needed, and even then, expect random failures.

  • Heaven forbid your ISP decides to CG-NAT your connectionā€”because then youā€™re screwed.

šŸ’€ 4. Performance is a Joke

  • IPsec does not handle packet loss or latency well.

  • A single flaky connection can cause timeouts, resets, and massive performance degradation.

  • If youā€™re using IPsec over a high-latency link, prepare for an awful user experience.

šŸ’€ 5. It Breaks Everything Else

  • Need VoIP to work? Good luck.

  • Need multiple tunnels with dynamic endpoints? Youā€™re in for a ride.

  • Need to fail over seamlessly? Not happening.

And if you think vendor-certified equipment makes it betterā€”think again. Even big names like Cisco, Fortinet, and Palo Alto have their own weird IPsec quirks.

Which means that a working config on one device will completely fail on another vendorā€™s boxā€”just to keep you on your toes.


The Solution | SD-WAN ā€“ The End of IPsec Pain

Now, imagine a world where you never have to debug another IPsec tunnel again.

Imagine secure site-to-site connectivity that just works, no matter the connection type, latency, or NAT situation.

Thatā€™s SD-WAN.

Why SD-WAN is the Holy Grail

āœ… No More IPsec Nonsense

  • SD-WAN doesnā€™t rely on fragile IPsec tunnels.

  • It uses smarter encryption mechanisms like DTLS or AES offloading, ensuring security without the hassle.

  • It establishes links dynamicallyā€”no more manually defining tunnel endpoints.

āœ… Seamless Failover

  • If an IPsec tunnel drops, the connection is dead until it renegotiates.

  • SD-WAN? It instantly fails over to a working path without dropping your sessions.

āœ… Handles NAT Like a Pro

  • SD-WAN doesnā€™t care if youā€™re behind NAT, CG-NAT, or double NAT.

  • It can leverage multiple WAN links and choose the best one automatically.

āœ… Better Performance

  • SD-WAN uses real-time traffic steering to choose the best path dynamically.

  • It prioritises critical applications, unlike IPsec, which just throws encrypted packets and hopes for the best.

āœ… Deploys in Minutes, Not Hours

  • With Fusionā€™s SD-WAN, you donā€™t need to manually configure encryption settings, phase 1, phase 2, or NAT rules.

  • Plug it in, connect it, and let it optimise itself.


Wrapping up with some Final Thoughts | SD-WAN = Peace | IPsec = Suffering

If you enjoy debugging logs, spending hours tweaking settings, and questioning your life choices every time a VPN breaksā€”by all means, keep using IPsec.

But if you want to actually get work done, maintain your sanity, and enjoy networking again, then ditch IPsec and switch to SD-WAN.

Fusionā€™s SD-WAN gives you:
āœ… Secure networking without the headaches
āœ… Seamless failover with no dropped sessions
āœ… Flawless NAT traversal with zero configuration stress
āœ… Real-time optimisation for superior performance

Itā€™s time to stop suffering. Ditch IPsec. Deploy SD-WAN. Get your life back.

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Written by

Ronald Bartels
Ronald Bartels

Driving SD-WAN Adoption in South Africa