Target's 2013 entry into Canada through the acquisition of Zellers store leases was one of the most costly retail expansions in North American history. The company opened 133 stores in under two years, significantly ahead of the operational readiness of its supply chain, inventory management, and systems infrastructure in the Canadian market. Persistent stockouts, pricing inconsistencies versus the U.S. Target experience, and an underdeveloped brand presence in a market with high consumer expectations drove sustained losses. Target exited Canada in 2015 after accumulating approximately $2 billion in losses and filing for creditor protection for the Canadian subsidiary — a failure that demonstrated the dangers of expansion speed exceeding operational preparation.

Target's 2013 data breach — which exposed 40 million payment card records and 70 million personal information records — was enabled by a technology infrastructure that had not kept pace with the scale of customer data the company was managing. The company's cybersecurity systems failed to act on automated alerts that could have detected the intrusion earlier. The breach cost over $200 million in direct expenses and years of customer trust recovery, and represented the consequence of systematic underinvestment in technology infrastructure relative to business scale. The episode accelerated Target's subsequent $7 billion technology and operations investment but came at significant cost.

Target entered fiscal 2022 with elevated inventory in discretionary categories — home, apparel, and seasonal goods — based on demand forecasts that underestimated the speed and magnitude of the post-pandemic consumer spending shift from goods back to services. The resulting markdown necessity, combined with elevated freight costs and supply chain expenses, compressed gross margin by approximately 4 percentage points and reduced operating income by over 50%. While the company's decision to take the markdown pain quickly rather than carry excess inventory was strategically sound, the forecasting failure itself reflected the difficulty of demand planning across a broad, discretionary-heavy category mix during a period of unprecedented consumer behavior volatility.

Despite launching target.com in 1999, Target was slower than optimal in building the digital ordering, fulfillment, and customer data infrastructure that would eventually become central to its competitive model. The company outsourced its e-commerce fulfillment to Amazon from 2001 to 2011 — a decision that prioritized short-term cost efficiency over long-term capability building — and spent the subsequent decade closing the digital infrastructure gap that the outsourcing arrangement had created. The delayed investment in proprietary digital capabilities allowed Amazon to deepen consumer digital shopping habits during the period when Target was not competing effectively in the channel.