A guide to timing, bundling, and personalisation so customers don’t feel “upsold to death”

Ancillaries have a perception problem. Customers like choice, convenience, and peace of mind. What they don’t like is feeling ambushed at checkout by a wall of add-ons that look suspiciously like “things you forgot to charge me for”.

The good news: ancillary fatigue isn’t inevitable. It’s usually a design problem, not a product problem.

This post is a practical guide to offering more without annoying people. We’ll cover timing, bundling, and personalisation, plus a few simple rules that reduce friction and protect conversion.

What ancillary fatigue looks like (and why it happens)

Ancillary fatigue shows up as:

  • Customers rushing past every option, even the useful ones.
  • Drop-offs right before payment.
  • More “hidden fees” complaints, even when nothing was hidden.
  • Lower attachment rates across the board, not just for one product.
  • Increased customer support queries, because people didn’t understand what they bought.

It happens when customers feel three things:

  1. Overwhelmed: too many choices, too little clarity.
  2. Distrustful: “Why am I only seeing this now?”
  3. Manipulated: urgency tricks, guilt copy, or defaults that feel sneaky.

Your aim is simple: make add-ons feel like service, not sales.

Timing: offer the right thing at the right moment

Most fatigue comes from asking for too much, too early.

A better approach is to map ancillaries to the customer’s journey and emotional state:

The three best moments to offer ancillaries

Moment A: When intent is highest (during selection, not at the end)
If someone is choosing a fare, room, or ticket type, they’re already making trade-offs. That’s when “flexibility” add-ons feel natural, not bolted on.

Moment B: Right after purchase (the “I’ve committed” moment)
Once payment is done, customers are more open to helpful upgrades because the pressure is off. This is a great place for travel utilities like eSIM, lounge access, carbon offsetting, transfers, or baggage-related support.

Moment C: When risk becomes real (pre-trip reminders and disruption moments)
As the departure/event date approaches, the customer’s mindset shifts from excitement to logistics. That’s when relevance spikes for services such as baggage delay compensation, flight delay compensation, or last-mile transport.

Timing rule of thumb

Checkout should be the cleanest part of your flow.
If your checkout page looks like a supermarket aisle, expect supermarket-level trust.

Bundling: fewer decisions, clearer value

Bundling works when it reduces decision load, not when it hides complexity.

The “3 bundle” model that avoids fatigue

  1. Core (always relevant)
    One or two universally useful options that align with the purchase itself.
    Example: “Make this booking refundable” or “Add protection for unexpected circumstances.”
  2. Contextual (relevant to this customer or trip)
    Driven by signals like destination, trip length, party size, fare class and seasonality.
  3. Utility (nice-to-have, post-purchase)
    Convenience add-ons that feel like helpful extras rather than insurance-adjacent products.

Bundling do’s and don’ts

Do:

  • Bundle around a customer goal: flexibility, connectivity, comfort, sustainability.
  • Keep bundles small and explain what’s inside in plain language.
  • Show the value in one line, then allow “learn more”.

Don’t:

  • Bundle random things because they have margin.
  • Make customers compare six bundles with tiny differences.
  • Use “Best Value” labels if the bundle isn’t genuinely best for most people.

Personalisation: relevance beats persuasion

Personalisation is not “how do we sell more?” It’s “how do we show less, but better?”

The best signals for personalisation (without being creepy)

Use signals that customers expect you to use:

  • Trip value (higher value = higher appetite for flexibility)
  • Time to departure (closer = higher risk perception)
  • Party size (families hate uncertainty)
  • Destination / seasonality (weather, peak disruption periods)
  • Fare type / room type (premium customers expect control)

Avoid personalisation that feels invasive:

  • Referencing personal life details.
  • Overly specific “we noticed you…” language.

Personalisation rule of thumb

If you can’t explain why an ancillary is shown in one sentence, it probably shouldn’t be shown.

The UX patterns that reduce fatigue fast

You don’t need a redesign. You need fewer friction points.

Pattern 1: “One primary, one secondary”

Give customers:

  • One main option (most relevant)
  • One alternative (for a different preference)
    Everything else can move post-purchase.

Pattern 2: Make the default neutral

Pre-ticked boxes, forced toggles, or guilt copy can lift short-term attachment, but they also increase complaints and refunds over the long term.

Trust scales better than tricks.

Pattern 3: Clarity beats copywriting

Use:

  • Plain language
  • One benefit-led headline
  • One short “what it covers”
  • One short “what it doesn’t”
  • A link to details

Customers don’t mind add-ons. They mind confusion.

Pattern 4: Show outcomes, not features

Instead of: “Includes X, Y, Z”
Try: “If plans change unexpectedly, you can get money back quickly.”

Outcomes feel like service.

The content checklist: what customers need to feel good about saying “yes”

Before you ship any ancillary, make sure customers can answer:

  • What is this, in one sentence?
  • When would I use it?
  • What does it cost and why?
  • What’s excluded?
  • How do I get help?
  • How fast is the outcome?

If any of these are unclear, attachment will suffer and fatigue will rise.

Metrics that tell you you’re causing fatigue (before customers do)

Don’t just track attach rate. Track health.

Watch:

  • Checkout abandonment rate (especially step-to-step)
  • Time on page (a spike can mean confusion)
  • Scroll depth / interaction rate (lots of hovers, few clicks can mean distrust)
  • Post-purchase cancellations and chargebacks
  • Support contact reasons (keyword clusters: “refund”, “charged”, “didn’t mean to”)
  • NPS / CSAT dips after checkout changes

A small attach-rate lift isn’t worth a long-term trust hit.

8) A simple framework to keep you honest: R.E.S.T.

Before launching an ancillary, ask:

R: Relevant
Is it genuinely useful for this customer, on this trip, right now?

E: Easy
Can they understand it in 5 seconds?

S: Safe
Does it feel transparent and fair, with no “gotchas”?

T: Timed well
Is this the right moment in the journey?

If you can’t tick all four, move it later or simplify it.

The takeaway

Customers aren’t “anti-ancillary”. They’re anti-friction, anti-confusion, and anti-feeling-played.

When you treat ancillaries like a service design challenge, you get the best of both worlds:

  • Higher conversion
  • Better attachment on the right products
  • Fewer complaints
  • More trust
  • Better long-term value

Because the real win isn’t selling more add-ons.
It’s selling the right add-ons, in a way customers actually appreciate.

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