Your Mid-Season Holiday Shipping Checklist

Cyber Monday may be over, but the real shipping pressure is just beginning. December brings a different kind of chaos: porch piracy climbs, delivery variability increases, customer expectations tighten, and support teams feel the strain. The good news? A few mid-season adjustments can stabilize your operation and prevent late-December headaches before they start.

Below is your practical mid-season shipping checklist; a set of quick wins you can put in place today to protect packages, reduce customer anxiety, and keep fulfillment moving.

Let’s start with the simplest fix that has the biggest impact on customer confidence. 

1. Turn on branded tracking and real-time alerts 

In December, customers care more about visibility than speed. Branded tracking and automated alerts help reduce “Where is my order?” tickets and give shoppers a reliable source of truth during the busiest weeks of the year. 

Mid-season must-dos: 

• Enable branded tracking pages so customers always know where their package is. 
• Turn on SMS and email delivery alerts to proactively reduce support volume. 
• Offer estimated delivery dates (even approximate ones help set expectations). 
• Use delay notifications to keep customers informed before frustration sets in. 

Learn more about Advanced Tracking. 

Once customers know where their packages are, the next priority is protecting the package itself, especially during the highest-risk weeks of the year. 

2. Protect every package with Guard

December is the highest-risk month for package loss, damage, and theft, and customers have little patience for uncertainty this time of year. A strong protection layer keeps support teams focused, refunds moving, and shoppers confident.

Mid-season must-dos:

• Enable automated USPS claims so your team isn’t filing paperwork manually during peak volume.
• Streamline FedEx claims by managing everything through a unified workflow.
• Add coverage instantly with the Shipping Insurance API at the moment you create the label.
• Reduce customer anxiety with Norton Shopping Guarantee, which protects against loss, damage, and porch piracy at no cost to merchants.

Together, these tools give you one protection layer that works quietly in the background, exactly what you need during the busiest stretch of the year.

Learn more about EasyPost Guard. 

With your protection foundation in place, the next step is preventing delays before they happen. That starts with cleaner address data.

3. Clean up address issues before they create delays

Address problems are one of the most preventable causes of late deliveries in December. With more gift shipments, more manual entry, and more first-time buyers, small errors multiply quickly. A single missing apartment number or mistyped ZIP code can turn into a multi-day delay, which is exactly what customers don’t want during the holidays.

Mid-season must-dos:

• Validate addresses at checkout to catch apartment numbers, unit details, and typos.
• Standardize international formatting to prevent customs or carrier rejections.
• Flag high-risk addresses for manual review before fulfillment.
• Reduce last-mile reroutes and return-to-sender shipments with early verification.

Taking a few minutes to strengthen your address hygiene now will save hours of late-December troubleshooting.

Learn more about the EasyPost Address Verification API. 

Once your data is clean, the next opportunity to avoid mid-season stress is choosing the right shipping services. 

4. Reassess carrier service levels to avoid mid-season cost spikes

Mid-December is when shippers tend to overspend. Tight delivery windows, shifting carrier capacity, and rising customer expectations often push teams toward faster and more expensive service levels. But with the right visibility, many orders can still arrive on time without premium costs.

Mid-season must-dos:

• Compare carrier service levels daily to avoid unnecessary upgrades.
• Shift volume between carriers when certain networks begin to slow.
• Use regional or hybrid services when they offer equal speed at lower cost.
• Monitor performance trends to adjust routing before delays hit your customers.

Optimizing your mix of carriers helps you control cost and maintain on-time delivery.

Learn more about Luma. 

Once your carrier strategy is tuned for mid-season conditions, the next step is keeping your warehouse operation aligned with fast-moving carrier cutoffs.

5. Review warehouse cutoffs and internal SLAs

The busiest weeks of the season demand tight coordination inside the four walls. Missed cutoffs, slow order flow, or unclear ownership can create delays that no carrier can fix. Ensuring that your warehouse teams are synchronized with the latest expectations prevents backlogs from snowballing.

Mid-season must-dos:

• Confirm updated carrier cutoffs and communicate them clearly across teams.
• Review internal “order to ship” targets and reinforce accountability.
• Audit bottlenecks that slow down picking, packing, or staging.
• Clear any backlog early so small delays now don’t become major issues later in December.

Keeping fulfillment aligned with real-world capacity gives every package a better chance of arriving on time.

With your warehouse running smoothly, it’s time to focus on the next major pressure point of December: handling returns efficiently before the post-holiday rush begins.

6. Simplify your returns process before the surge hits

Holiday returns start earlier than most teams expect. Gifts shipped in early December often come back before Christmas, and the week immediately following the holiday is one of the busiest return periods of the entire year. Preparing now prevents the bottlenecks and customer frustration that typically accompany late-season returns.

Mid-season must-dos:

• Enable automated return labels so customers can self-serve instead of contacting support.
• Offer a clear, branded return experience so shoppers can track returns as easily as outbound packages.
• Pre-define rules for returns routing to keep warehouses and stores from getting overwhelmed.
• Use analytics to identify high-return SKUs and adjust product detail pages where appropriate.

A smoother return process keeps customers satisfied and reduces pressure on support teams when volume peaks.

Learn more about WeSupply Labs. 

As returns rise, so do claims. Automating this final layer of protection now will save hours during the busiest stretch of the season.

7. Automate claims to reduce December workload 

December always brings an increase in damaged, delayed, and missing packages. Manually filing claims during the busiest month of the year drains your team’s time and slows customer refunds. Automating the process keeps everything moving and gives support teams time back when they need it most.

Mid-season must-dos:

• Use automated USPS claims to manage documentation and filing without extra manual steps.
• Centralize FedEx claims alongside USPS so your team isn’t juggling multiple portals.
• Track claim status in one dashboard to accelerate customer communication.
• Reduce rejected claims with automated documentation checks and consistent submission workflows.

When claims resolve faster, customers receive refunds sooner, freeing your team to stay focused on fulfillment, not paperwork.

Learn more about automating your USPS claims. 

With claims under control, the final step is keeping customers informed. Proactive communication is your best defense against late-season stress.

8. Communicate proactively with customers

When delivery timelines tighten and support volume rises, clear communication becomes one of your strongest tools. Setting accurate expectations before customers have to ask reduces pressure on your support team and helps maintain trust during the busiest weeks of the year. Proactive updates also minimize frustration when carriers experience delays outside your control.

Mid-season must-dos:

• Update your shipping FAQ with current cutoff dates and expected delivery windows.
• Add on-site banners to highlight delays, deadlines, or high-volume periods.
• Automate delivery and delay notifications to keep shoppers informed without manual outreach.
• Make returns instructions easy to find and simple to understand.
• Use branded tracking to give customers a single, reliable source of truth throughout their delivery journey.

Clear communication is one of the simplest ways to strengthen the customer experience when things get busy.

With proactive communication in place, you’re ready to bring all the pieces of your mid-season strategy together.