Shipping Automation: What to Automate First (and Why the Order Matters)

2026 Edition · 9 min read · By the ShippyPro Product Team

If you're shipping 5,000+ orders per month, you've already felt the moment your operation shifts from manageable to fragile. Your team is burning hours on repetitive tasks. Mistakes are creeping in. And every time you think about scaling to 10K orders per month, you quietly wonder whether your current process can survive it.

The answer is automation. But here's the problem most merchants run into: shipping automation platforms can do almost everything — which means most teams either automate nothing (overwhelmed by options) or automate the wrong things first and don't see meaningful results.

This guide gives you the right order. Not based on what's technically possible. Based on what actually saves time, reduces errors, and lets you scale without adding headcount.

The framework: automate in this exact order

Every shipping operation is different, but the priority logic is universal. When you're managing thousands of orders per month, automation ROI follows a clear hierarchy:

First: Automate what wastes the most time → immediate capacity unlock. Second: Automate what causes the most errors → reduce support load and carrier chargebacks. Third: Automate what blocks you from scaling → remove bottlenecks before they become critical.

Here's what that looks like in practice — step by step, in order.

Priority 1: Label generation and carrier selection

This is where to start. No exceptions. At 5,000 orders per month, your team is manually reviewing each order, deciding which carrier to use, selecting a service level, and generating the label. That process burns 40+ hours of labor monthly. At 10,000 orders per month, it becomes unsustainable.

1. Build carrier selection rules based on destination and weight

The goal: zero manual carrier decisions for standard orders. Your team should only be choosing carriers when an order falls outside your defined rules — not for the 80% of orders that are completely normal.

Start with simple rules. "Orders to the UK under 2kg → Royal Mail. Orders over 2kg → DHL." "Orders going to EU countries → DPD. International orders outside EU → FedEx." These two rules alone might cover the majority of your daily volume. You can add complexity later. ShippyPro's AI automation evaluates destination, weight, dimensions, and order value simultaneously — and selects the right carrier in milliseconds without any manual review.

2. Automate service level selection

Express for orders flagged as urgent. Standard for everything else. The rule should be automatic — not a judgment call your team makes on each order. Connect service level selection to your checkout data: if the customer paid for express at checkout, the label should reflect express automatically without anyone checking.

3. Set up automatic parcel assignment

Define your standard box sizes and their weight/dimension thresholds. Let the system assign the right packaging based on product dimensions rather than having your fulfillment team decide each time. This also eliminates dimensional weight surcharges caused by using oversized packaging by default.

4. Enable batch label printing

Once carrier selection and service levels are automated, batch printing is the natural next step. Generate and print 500 labels with one action instead of one at a time. At 200 orders per day, single-label printing at even 30 seconds per order is 100 minutes of pure manual time daily — eliminated completely.

Priority 2: Address formatting and validation

Customers enter addresses in creative ways. Missing apartment numbers. Typos in street names. Wrong postal codes. Each of these creates a cascade of costs: failed delivery, returned package, carrier surcharge, support ticket, reship cost, and a frustrated customer. Automating address validation prevents the entire chain.

5. Enable address standardisation on label creation

Different carriers have different address formatting requirements. USPS requires all caps. Some carriers strip special characters. "Street" versus "St" versus "Str." matters to some carrier systems. Automated standardisation reformats every address to meet the requirements of whichever carrier is being used — without your team touching it.

6. Add validation before labels print

The critical rule: validate addresses before the label is created, not after. A flag at label generation stops the problem. A flag after the package has already been handed to the carrier is too late. Configure your automation to either auto-correct common errors (transposed postal code digits, missing apartment numbers derived from order history) or flag the order for human review before it ships.

7. Clean up customer info formatting automatically

Phone number formats vary wildly by country. Company names sometimes contain characters that carrier systems reject. Names with accents or special characters cause issues with certain carriers. Automated formatting at the point of label creation catches these before they become carrier rejection errors — without your team reviewing every field manually.

Priority 3: Order notes and special handling

Some orders need treatment that standard fulfillment doesn't cover: gift wrapping, fragile handling, specific packing instructions. If these requirements aren't surfaced clearly and automatically, they get missed. If they're surfaced manually, someone has to read every order and flag exceptions — which doesn't scale.

8. Auto-tag orders based on attributes

Define the attributes that trigger special handling — gift message present, fragile product SKU, subscription order, wholesale customer — and let the system apply tags automatically. Orders with gift messages get tagged "GIFT WRAP" without anyone reading the order notes. Orders containing fragile product SKUs get tagged "HANDLE WITH CARE" without a fulfillment manager reviewing product categories.

9. Write handling instructions directly to labels and packing slips

Don't rely on a separate tagging system your fulfillment team needs to check. Configure automation to write handling notes directly on the shipping label or packing slip that travels with the order. The instruction is on the physical document in the box — impossible to miss, impossible to forget to check.

10. Flag rush orders for same-day fulfillment automatically

Express and next-day orders should hit your fulfillment queue at the top, automatically, without a manager manually sorting the pick list. Connect urgency flags to your carrier selection rules from Priority 1: if an order is flagged as rush, the rule already knows to select express service — the two automations work together.

Priority 4: Multi-carrier rate shopping

This is optimisation, not survival. You can operate without it — but you're leaving real money on the table. Once label generation and address validation are running cleanly, rate shopping is the next obvious ROI unlock.

11. Enable real-time rate comparison across all your carriers

If you have contracts with multiple carriers — DHL, DPD, Evri, UPS — their rates vary by destination, weight, dimensions, and service level. Manually comparing rates for every shipment is impractical, so most teams pick one default carrier and overpay on a significant percentage of their volume. Automated rate shopping pulls live rates from all connected carriers and selects the cheapest option that meets your delivery requirements — every time, with no manual comparison.

12. Build rule-based overrides on top of rate shopping

Rate shopping isn't always "cheapest wins." Sometimes you have carrier commitments that require minimum volume. Sometimes specific destinations have a preferred carrier for reliability reasons. Build overrides: "Always use DHL for shipments to Germany, rate-shop for everything else." "Never use Carrier X for orders over £500 — use Carrier Y regardless of price." The rules contain the rate shopping; they don't replace it.

13. Optimise for delivery speed vs. cost automatically

If a standard service delivers in 2 days and an express service delivers in 2 days to the same destination — because express is the standard for that route — you shouldn't be paying express rates. Configure your rate shopping to factor in actual transit time alongside cost, so you're paying for speed only when it actually results in faster delivery. ShippyPro's Optimizer handles this comparison automatically across your full carrier mix.

Priority 5: Customer notifications

Customers want to know where their order is. If you're not proactively sending tracking updates, you're fielding support tickets — each one costing agent time to look up the order, find the tracking status, write a response, and handle any follow-up. If you're sending updates manually, you're wasting time that automation should own.

14. Automate shipping confirmation the moment a label is created

As soon as the label prints, the customer should receive a shipping confirmation with their tracking number and estimated delivery date. Not in a batch at the end of the day. The moment the label exists. This single notification eliminates the "has my order shipped yet?" inquiry almost entirely — because customers know the answer before they think to ask.

15. Set up out-for-delivery and in-transit alerts

The out-for-delivery notification is the highest-impact message in your entire notification stack. Research shows 36% of failed deliveries happen simply because the recipient wasn't home. A well-timed "your package is arriving today" alert lets customers arrange to be available, ask a neighbour, or redirect to a pickup point. Configure this to send via SMS or WhatsApp — not email. This is time-sensitive. It needs to arrive and be seen within minutes, not hours. ShippyPro Track & Trace handles multi-channel notification routing automatically.

16. Add exception notifications for delays and delivery failures

When something goes wrong — a delay, a failed delivery attempt, a customs hold — the worst thing you can do is nothing. 70% of customers won't repurchase after a failed delivery experience, but the research consistently shows the driver is the silence, not the failure itself. Configure automated exception notifications that tell the customer what happened, what happens next, and what (if anything) they need to do.

17. Send delivery confirmation with a review request

The moment of delivery is when customer satisfaction peaks. It's your highest-converting moment for review requests — dramatically outperforming review campaigns sent days later. Configure a delivery confirmation email that includes a short review link. Set it once. It runs automatically for every delivered order.

Priority 6: Returns processing

Returns are lower volume than outbound shipments — typically 5–20% of orders depending on your category — but they're disproportionately time-consuming. Each return touches multiple systems, requires manual coordination, and generates customer anxiety while in-flight. Automating returns creates a dramatically better customer experience and frees your team from coordination work that adds no value.

18. Launch a self-service returns portal

The customer initiates the return, selects a reason, and receives a return label automatically — without anyone on your team getting involved. The label is generated based on return reason and destination, the right carrier and service level are selected, and the customer is told exactly what to do next. No email chains. No waiting for a response. No manual label generation. ShippyPro Easy Return provides a branded self-service portal that handles this entire flow out of the box.

19. Connect return tracking to inventory and refund systems

When the return arrives at your warehouse, the inventory update and refund trigger should happen automatically — not after someone manually scans the package and updates three systems by hand. Connect your returns automation to your inventory management and payment system so the moment a return is confirmed received, the downstream processes fire without human intervention.

What not to automate first

As important as the priority order is what to avoid. These are the three most common mistakes teams make when starting with shipping automation.

❌ Don't start with edge cases

"We need automation for orders going to the Channel Islands with a fragile product and a gift message over £200." That is not where you start. Automate the 80% of standard orders first. Edge cases account for a small fraction of your volume — solving them before you've automated the majority is a guaranteed way to spend weeks configuring rules that affect five orders a day while your team still manually processes hundreds.

❌ Don't automate reporting before operations

Dashboards and analytics are satisfying. They make shipping feel managed. But if your team is still manually creating labels, reporting automation is noise. Fix the operations that affect every order before building visibility into those operations. The metrics become meaningful when the underlying process is automated — not before.

❌ Don't over-engineer your rules on day one

Start simple. "Orders under 2kg to Europe → Carrier A. Everything else → Carrier B." Two rules. You can add complexity later once you see what the system catches and what it misses. Teams that try to encode every possible scenario into their carrier selection rules on week one invariably spend more time debugging the rules than they would have spent making manual decisions. Build simple. Observe. Add complexity only where the data shows you need it.

How to implement this without disrupting your current operation

The practical reality: most teams know what to automate but get stuck on how to set it up without breaking a process that, however imperfect, is currently shipping real orders to real customers.

20. Start with one workflow — carrier selection and label generation

Pick the highest-volume task and automate just that. Don't touch anything else until this is stable. Within ShippyPro's Shipping Platform, pre-built automation templates handle common carrier selection scenarios — start with a template and customise it rather than building from scratch. Most merchants are live with their first carrier selection rules within a single working session.

21. Test on a small batch before going live

Run your automation on 20–30 orders manually selected to cover your typical order mix before activating for all orders. Verify it's selecting the right carriers, formatting addresses correctly, assigning the right service levels. Check the edge cases you're most concerned about. Then activate. Don't go live blind.

22. Set a two-week review checkpoint

After two weeks, check: Is the carrier selection working correctly? Are there order types hitting the wrong rule? Are there addresses slipping through validation that shouldn't? Automation is not "set it and forget it" — it's "set it, test it, improve it." Build a two-week review into your implementation plan from the start, not as an afterthought.

23. Layer on the next workflow only when the first is stable

Once carrier selection has been running cleanly for two weeks, activate address validation. Once address validation is stable, configure special handling rules. Work through the priority list sequentially. Each layer builds on the stability of the previous one — and your team has time to adapt to each change before the next one arrives.