Twenty Years with a Pen: How Apple Accidentally Escaped Tablet Mediocrity

tablet

By James Wilt, Iasa Distinguished Architect

Anyone who knows me knows that tablet computers have long been one of my defining passions in this industry. My journey took root in 2003 building applications on the Compaq TC1000 slate tablet. Many advancements in the platforms and the solutions I developed occurred over the next 8-9 years. My October 2010 blog post documents this period and the progression of tablets during that time.

In 2015, I literally gave up the keyboard totally for the pen and I’ve never looked back. For the past decade, the pen & screen have been my gateway into everything from cloud computing to AI, coding, and writing. Along the way, I’ve seen both remarkable advancements and frustrating setbacks. Today, I want to share my perspective and opinion on where tablets currently stand (this is intentionally subjective, not scientific).

I regularly rotate between three daily devices: my Samsung Galaxy Tab 9 Ultra (Android 15/One UI 7), my Microsoft Surface Pro 10 (Windows 11), and my Apple iPad Pro 5th Gen (iPadOS 26). This keeps me from stagnating on a single platform. I code, brainstorm, and even wrote a 32,000-word novella entirely on these devices without a keyboard, leveraging their handwriting interfaces and pushing their productivity capabilities. My natural biases lean toward Android and Windows, but my observations span all three ecosystems.

The Harsh Reality of Tablets

Let’s be clear: tablets are still second-class citizens at all three of these and most every vendor. Phones and laptops dominate their priorities, leaving tablet users to fight for scraps. Reporting bugs or asking for support feels like shouting into a black hole while pulling teeth from a cat – painful, frustrating, and unrewarding. It is blatantly obvious that the teams assembling these platforms, operating systems, and software apps are only occasional tablet users. Failures in continuity and usability are obvious and persistent from one release to the next.

Mainstream groupthink is also an occasional tablet user – you know who you are – the media forcing vendors to integrate AI into their platforms before fixing their platforms. So, vendors bolt-on AI to their browser instead of making their handwriting and selecting text work better to get groupthink approval for their AI advancement. Embarrassing.

Over time, I’ve adopted a pragmatic stance: learn the workarounds, celebrate the rare improvements, and accept that “mediocre” may be the best these platforms will ever offer… until recently.

There never has been a clear leader in this space. Each offered their own flavor of mediocrity. But something has shifted. Let’s unpack this.

Samsung

Samsung has consistently led the field in hardware and pen integration. Their tablets boast stunning displays, smudge-resistant glass, and pen functionality that seamlessly extends across both tablet and phone – an experience unmatched elsewhere. Handwriting with Samsung’s keyboard has the right features (transparency, direct pen input, swiping), but its execution pales next to Google’s Gboard, which remains the gold standard for handwriting input on Android.

On the software side, Samsung’s One UI has set the bar for tablet multitasking. Its windowed interface rivals Windows, eclipses Apple’s Stage Manager, and offers a far more intuitive paradigm for real productivity. One UI was enough to make me overlook Android’s chronic weakness: poor-quality apps compared to Windows and iPadOS.

But then came One UI 7. Instead of pushing forward, it deprecated useful features, introduced few meaningful improvements, and launched with bugs ranging from lock-screen failures and privacy lapses to UI lag and degraded camera quality. The rollout was so problematic that Samsung was forced to pause and rework it, delaying its release for months.

The bigger problem, though, lies beyond Samsung’s control. The Android tablet app ecosystem is abysmal. In many cases, the phone versions of apps (including Microsoft Office as most of us know it) are more polished and feature-rich than their tablet counterparts. With One UI 7 stumbling, Samsung’s once slight edge in this “mediocrity race” slipped greatly. That’s unfortunate because their hardware deserves better.

Microsoft

For a moment in history, Windows tablets had their chance to dominate. When the iPad launched without a pen, serious business users still gravitated to Microsoft. It was theirs to win, but they lost it quickly. Within a year, Windows tablets’ previously acceptable poor battery life, screen resolution, and overall responsiveness were darkened by the iPad’s superior hardware and seamless usage continuity.

Still, credit where it’s due: even with subpar hardware (and a fan that loves to scream), the Surface pen experience remains competitive, nearly on par with Samsung’s – albeit dated in accuracy. Windows tablets are perpetually “almost there,” brimming with such potential that is just out of their reach. Some aspects shine. Transparency effects in Windows’ on-screen handwriting keyboard and UI elements are superior even to Samsung’s implementation.

One saving grace for Windows is Remote Desktop (now, Windows App) where Android and IPadOS tablets can connect and run Windows remotely. It’s a saving grace because all the pen & tablet inconsistencies and flaws inherit to Windows tablet native use are buffered and the experience is far richer when run remotely from one of these other tablets who also offer higher remote screen resolutions than Windows native hardware.

Microsoft’s broader strategy seems uninterested in tablets. As their apps evolve, many feel increasingly hostile to pen input. For example: in the New Outlook, the search field cannot be tapped into and text entered with a pen – you literally need a mouse & keyboard to use it. Unlike the other platforms where they work in harmony, Windows pen & touch interactions are different, inconsistent, and often far from intuitive.

Microsoft’s sprawling focus on so many other shiny objects in the industry may prevent them from ever reclaiming leadership in this space leaving them in the “me-too” mediocre zone.

Apple

Apple has long been the classic disruptor – ignoring mainstream criticism while pursuing its own path. But with iPad, their strategy has been marred by hesitation. Years of internal debate postponed the Pen (oops, I mean Pencil) and delayed serious multitasking capabilities. As a result, iPads have hovered in that same mediocrity bubble, saved only by apps that often outclass their desktop equivalents (Office & OneNote on iPad are some of the best experiences) and strong hardware (albeit with smudge-prone glass).

For years, I gave up on the iPad as a serious pen-based productivity platform. Attempts at multitasking felt half-baked compared to Samsung’s One UI. I mostly used Jump Desktop to remote into my Windows or Mac systems as it was a far richer experience with substantially higher screen resolutions available through the iPad.

All this changed with iPadOS 26. It is unmistakably influenced by One UI – yet refined in ways one has grown accustomed to expect from Apple.

Accidental Escape from Mediocrity

My perfect tablet would combine Samsung’s hardware and interface innovations, Windows’ transparency and productivity roots, and Apple’s unparalleled app ecosystem… This is mostly possible with iPadOS 26.

It’s far from completely perfect. Handwriting input is still an afterthought, and serious tablet professionals will be sure to identify remaining gaps. However, for the first time in a decade, Apple has pushed iPad beyond the mediocrity bubble where the others remain. One might argue it was intentional, but Apple’s errors from its earlier attempts – its original Pencil to Stage Manager – assures they are wholly capable of totally missing the mark – yet – willing and able to learn from prior failures to eventually get it right.

It took 10 years for the industry to get here. I expected Samsung or Microsoft to lead the way, but Apple has quietly broken through first. Good on them.

Tablets have long promised greatness while only delivering “good enough.” With iPadOS 26, Apple has finally nudged the platform closer to its potential. Whether others follow remains to be seen, but for the first time in years, the future of tablets feels genuinely exciting again.