Can AI Recognize Living Structure?

Sitting area in the Parents' Realm of the Sala House - Christopher Alexander, Architect (photo by Ekyono; file is licensed under the Creative Commons Attribution-Share Alike 4.0 International license).
 

For years I’ve wondered what role AI might play in architectural design—not in the routine domains of optimization, code compliance, or energy modeling, but in the harder question of how buildings acquire coherence, depth, and human resonance. Much of the current discourse avoids that question. It gravitates toward what is measurable and leaves the deeper structure of design unexamined.
 
That deeper question repeatedly leads me back to Christopher Alexander’s work and, more recently, to Nikos Salingaros’s explorations of whether large language models can detect “living geometry” in buildings.
 
Alexander identified fifteen fundamental properties that tend to co‑occur in environments we experience as alive. These appear in nature, in traditional buildings, and in the artifacts people cherish. They are not stylistic devices but a system of interdependent relationships:
 

• Levels of scale

• Strong centers

• Thick boundaries

• Alternating repetition

• Positive space

• Good shape

• Local symmetries

• Deep interlock and ambiguity

• Contrast

• Gradients

• Roughness

• Echoes

• The void

• Simplicity and inner calm

• Not‑separateness

When these properties reinforce one another, the result feels coherent and grounded. Salingaros links them to human neurophysiology, arguing that our perceptual systems evolved to favor nested scales and relational order.
 
With this in mind, I tested an online tool called the 15 Fundamental Properties of Wholeness Analyzer by Danny Raede. It is an admirable initiative: open‑source, accessible, and one of the few attempts to operationalize Alexander’s ideas. But it arrives without documentation on training data, methodology, or weighting. Experimenting with it suggests a modest image classifier that can detect visual signatures such as symmetry, repetition, and contrast, but struggles with the relational, multiscalar depth Alexander’s framework demands. A model can recognize what local symmetry looks like; it cannot easily evaluate how that symmetry strengthens centers across scales or contributes to overall wholeness. These limits reflect the state of current vision models more than the ambition of the tool.
 

Portion of an analysis of the Sala House image, by Danny Raede's 15 Fundamental Properties of Wholeness Analyzer.

A deeper constraint applies to any image‑only system: a single photograph is never a building. It freezes one viewpoint, one moment, one lighting condition. Many of Alexander’s properties are inherently experiential. Thick boundaries reveal themselves in section. Gradients unfold in movement. Not‑separateness depends on context beyond the frame. Positive space requires reading the shape of the outdoor room. Judging wholeness from one static image is necessarily partial.

After using Raede’s tool, I wanted a more relational reading. I turned to a large language model (Microsoft Copilot) and prompted it to analyze the same images through the lens of the fifteen properties: “Consider relationships across scales, massing, thresholds, centers, voids, interlock, context, and overall coherence.”

The difference was immediate. The model produced something closer to the kind of relational analysis an architect might offer. It could do this because it was not limited to pixel‑level cues. It could integrate the image, the conceptual structure of the fifteen properties, and the contextual hints in the prompt. This does not overcome the limits of a single photograph, but it allows the model to make sense of the available information in a more integrated way than a vision‑only classifier can. 

Design for a renovation and expansion of the McMinnville Public Library (1982). The original Carnegie library is on the left; the proposed addition is on the right, which opens toward McMinnville City Park.

To illustrate, here is its analysis of my 1982 project for an addition to the Carnegie Library in McMinnville (completed during my time as a student in the University of Oregon’s architecture program), based on my design drawings and the photograph of the physical model I built, seen above:
 
"The project exhibits a remarkably coherent alignment with Alexander’s fifteen properties. Its organization unfolds through clear levels of scale—from the civic park and axial approach to the outdoor room, lobby, reading rooms, and smaller alcoves—each nested within the next. The original Carnegie library and the new addition form strong centers, stabilized by the cloister‑like outdoor room and the layered thresholds that create thick boundaries between inside and out. Exterior spaces are shaped as positive space rather than residual voids, and the interlock between old and new is handled with care: axes align, proportions echo, and the addition adapts to its context with an intentional roughness that reflects the site’s particularities. Gradients of enclosure and light develop through the sequence of plaza → cloister → lobby → reading rooms, while the repetition of structural bays, window groupings, and spatial rhythms creates subtle echoes across scales. The underlying parti—House of Reading and House of Books—gives the building a simplicity and inner calm, and the reciprocal relationship between the volumes expresses a genuine not‑separateness. The coherence of the whole arises not from stylistic gestures but from a relational structure that resonates strongly with Alexander’s fifteen properties."

A vision‑only classifier cannot produce this kind of relational reading.

These experiments raise a larger question: could any future tool reliably detect living structure? Even with far more capable models, the answer is probably no. Wholeness is emergent. It arises from iterative negotiation among site, program, structure, light, materials, craft, and human inhabitation. These relationships unfold across scales and through time. Many require embodied, situated judgment. AI may one day illuminate hidden patterns or diagnose coherence more reliably, but the deeper life of a building is unlikely to spring from software alone. Design remains a recursive field grounded in construction’s realities.

Even so, the potential is real. If future systems combine multiscale visual reasoning, spatial‑relationship understanding, datasets annotated for the fifteen properties, and insights from environmental psychology and cognitive science, AI could become a useful diagnostic partner. It might help architects see strengths, weaknesses, and missed opportunities. Whether Alexander’s properties remain the definitive rubric is debatable. They endure because they describe persistent, cross‑cultural patterns rooted in human perception. But they demand a relational intelligence that challenges even skilled humans to articulate fully. Any meaningful AI engagement with them will require moving beyond feature detection toward something closer to architectural judgment.

My own exploration echoes themes in Salingaros’s work on living geometry’s measurable effects on cognition and wellbeing. The takeaway is modest but clear: relational coherence in buildings is not an aesthetic preference; it has consequences for how people perceive and inhabit space. For now, AI’s most immediate value lies in conversation, as a tool that helps us see our work more sharply, test assumptions, and notice relationships we might otherwise overlook. In my experiments, it has already done that. If future systems can extend this capacity without losing sight of the relational nature of design, they may become useful partners in the ongoing effort to create environments that are coherent, grounded, and humane.

Dwelling Before Design

It is not uncommon for ideas encountered early in life to lie dormant for years before revealing how deeply they have shaped one’s thinking.

My introduction to the German philosopher Martin Heidegger came during my undergraduate years at the University of Oregon, when I enrolled in a course on existentialism. The decision was not entirely philosophical. My then‑girlfriend (now my wife) was also taking the class, and spending a few additional hours each week contemplating the nature of existence seemed like a reasonable trade-off.

That course introduced us to thinkers such as Jean‑Paul Sartre, Albert Camus, and Heidegger. At the same time, I was studying architecture under professors such as Bill Kleinsasser, whose emphasis on the experiential qualities of buildings resonated closely with what I was encountering in existential philosophy. The overlap between phenomenology, existentialism, and Bill’s approach to architecture left an early impression that would shape my thinking about architecture. It also planted an early awareness of the importance of continuity and the character of existing places.

Phenomenology, as I came to understand it, is less a theory than a discipline of attention. It asks us to consider how places are lived; for example, how light, material, proportion, and sequence shape our experience of being in the world. It is concerned with the felt qualities of environments: the way a room settles us, the way a path reveals or withholds, the way a building participates in the life around it. This emphasis on lived experience provided a conceptual bridge between the philosophy I was studying and the architectural education I was receiving.

Heidegger’s essay Building, Dwelling, Thinking expresses this connection memorably. He suggests that the relationship between building and dwelling is commonly misunderstood. We tend to assume that people construct buildings and then inhabit them. Heidegger proposes the reverse: human beings are dwellers first. Building arises from the human need to dwell in the world.

We do not dwell because we build. We build because we dwell.

For architects, that inversion carries profound implications. If the purpose of building is to support dwelling, then architecture cannot be understood merely as the production of objects. Buildings must instead be seen as places that sustain and enrich human life. In this sense, dwelling is the fit between people, place, and time.

Those early lessons did not announce themselves loudly in my day-to-day work, but over the years, I found that they quietly informed how I assessed projects, made design decisions, and responded to the character of places. The projects that seemed most successful were not necessarily the most visually striking. Nor were they the most technically ambitious. Rather, they were the ones that felt deeply rooted in their surroundings, places where the relationship between building, landscape, and human activity seemed natural and unforced.

Some architects have shown an especially strong instinct for this deeper purpose. What unites their work is not a recognizable style but a sensitivity to how buildings mediate our experience of place. Frank Lloyd Wright’s best projects grow out of their landscapes. Charles W. Moore—whom I had the good fortune to work alongside in the mid‑1980s—brought an extraordinary attentiveness to memory, ritual, and delight. He created places that were both deeply personal and deeply inhabitable. Even in its playfulness, his work was grounded in a phenomenological understanding of how people live in and move through space. Each, in a different way, begins with dwelling.

This emphasis on place is echoed in the writings of Christian Norberg-Schulz, who drew upon Heidegger’s phenomenology to articulate architecture as the creation of meaningful environments. He reminds us that architecture is not simply the assembly of materials, but the cultivation of places in which human life can unfold with coherence and significance.

My own professional path unfolded on a far more modest scale. Most architects spend their careers designing buildings that never appear in architectural surveys or glossy monographs. Yet the same fundamental question remains: does a building support the life that will occur within it? Does it contribute something meaningful to the place where it stands?

These questions gradually led me to appreciate the value of continuity in the built environment. Early in my career, I shared the profession’s typical enthusiasm for new construction. Over time, however, I found that communities responded most strongly to projects that preserved familiar patterns of use and memory, even when the changes were modest. These might take the form of better natural light in a longstanding community hall, improved accessibility in an aging civic building, or refreshed materials in a church sanctuary—interventions that allow the accumulated character of the place to persist and deepen rather than starting anew.

Here again, Heidegger’s thinking resonates. In Building, Dwelling, Thinking, building is not primarily an act of domination or transformation. It is an act of “sparing and preserving,” allowing places to retain their essential qualities even as they evolve.

Looking back, I can see that the philosophical threads introduced during my university years accompanied me throughout my career. The ideas encountered in that existentialism class, the experiential emphasis of professors like Bill Kleinsasser, and the place‑oriented perspectives of thinkers like Heidegger and Norberg-Schulz helped shape how I came to understand architecture—not simply as construction, but as the creation of places where human life can unfold meaningfully.

In the end, that may be the most enduring insight these thinkers offer. Buildings matter not because they stand, but because they help us dwell.

Anchovies, Bell Peppers, and Other Modest Truths

 

Food habits have a way of settling in over time. In my case, one such habit is a preference for anchovies and green bell peppers on a substantial-crust pizza. For my wife and me, Track Town Pizza has long been the go‑to pizzeria, tied to Eugene’s athletic culture as much as to its menu. None of this is remarkable, but it has been consistent for years.

A few years ago, I wrote about my weakness for chain restaurants. That weakness (or rather, comfort) has always been there. What I appreciate, whether in a chain or at Track Town, is predictability. It is the ease of knowing what will arrive at the table.

Cooking has never been my forte. When we cook, we prepare simple meals, nothing elaborate. Food tends to function more as routine than expression, our meals dependable markers in the day rather than creative projects. Now that I’m retired, that routine is more apparent, but it isn’t different.

Places can take on a similar role over time. Certain restaurants, streets, and buildings become part of the quiet structure of daily life. They may not be remarkable in themselves, but their familiarity is reassuring. You know how they work and what they offer. Their steadiness becomes part of the background, a reliable element in the pattern of daily life.

Most people have a few habits that stay with them. Mine happen to include anchovies and bell peppers. They are not fashionable, but they are consistent. That kind of familiarity has always been enough for me. It is simply what I like, nothing more.

How Company Alters the Measure of a Walk

View from the top of Mt. Baldy, along the Ridgeline Trail, Eugene (my photo).

I’ve been walking a lot lately, often in the company of two colleagues from my architectural life, fellow retirees Dave Guadagni and J.F. Alberson. We make the rounds of the usual places, including the Mt. Pisgah Arboretum, Dorris Ranch, Delta Ponds, the Ridgeline Trail, and the Amazon corridor. Most excursions cover four or five miles. These are familiar routes, ones we return to regularly. 

What I’ve noticed is how differently those same distances register depending on whether I’m alone or with company. On my own, I’m more aware of the length of things, be it the stretch between landmarks, the grade of a hill, or the time it will take to loop back. When it’s the three of us, the distance feels shorter. Conversation, a shared pace, and the occasional stop to look more closely at something alter the measure of the route. The walk becomes less about getting from one point to another and more about the ground between them. The end arrives sooner than expected. It isn’t only the miles that compress, but what we notice shifts as well. 

J.F. brings birding into the mix, which changes what comes into view. Avian species I’ve apparently been sharing space with for years—Belted Kingfishers, Pied-Billed Grebes, Brown Creepers, Ruby-crowned Kinglets, and more—suddenly register. He’ll pause and point out something I would have passed without a second thought. Nothing about the setting has changed, but my perception has. 

Retirement makes this rhythm possible. The days are more open, and the walks don’t have to be fitted into narrow margins of time. Familiar places can be revisited without urgency, simply to see them again. Repetition reveals small shifts: light striking the same bend of trail differently in winter than in summer, foliage thickening or thinning from week to week, and bird patterns subtly changing. The routes themselves are unchanged, but their reading is not. I’ve yet to see a beaver, an otter, or a fox along these paths, though I know they’re present, a reminder that there is still more to notice.

A Shift in the Civic Landscape

The former Wells Fargo building in downtown Eugene (Google Streetview).

The County’s recent purchase from Eugene School District 4J of the former Wells Fargo building at 99 E. Broadway marks a significant pivot. It signals the end of Lane County’s plan to site a new courthouse on the former Eugene City Hall block and the beginning of a more incremental approach to meeting the needs of the courts, the Sheriff’s Office, and the District Attorney. It also raises a larger question: what becomes of the City Hall block now that its intended purpose has evaporated?

Before considering that question, it’s worth recalling why the County pursued a new courthouse in the first place. The existing building (designed by the firm of Wilmsen & Endicott and completed in 1959) is a structure stretched far beyond its intended capacity. By the time the County undertook a scoping study in 2018–2019, several issues had become impossible to ignore.(1) The most pressing was security and circulation. Modern courthouses rely on three fully separated circulation systems: public, private (judges and staff), and secure (in‑custody defendants). The current building cannot provide this separation. Judges, jurors, victims, witnesses, attorneys, and in-custody defendants routinely cross paths in public corridors, compromising safety and dignity every day.

The structure and building systems also lag contemporary expectations. Mechanical, electrical, and life‑safety components have reached the end of their useful life. The building cannot support modern technology loads, accessibility standards, or seismic requirements. Courtrooms remain undersized and inflexible, unable to accommodate modern jury boxes, ADA-compliant circulation, or the spatial needs of today’s legal practice. Support spaces fall short. And the courthouse cannot expand. Streets and the Public Service Building hem it in, leaving no flexibility for comprehensive modernization.

The Oregon Judicial Department documented these issues, the presiding judge echoed them, and the 2018–2019 scoping process confirmed them. The accompanying conceptual design attempted to address these deficiencies comprehensively and propose a courthouse that met contemporary standards for safety, functionality, and civic presence. Voters rejected the bond measure, state funding disappeared, and the project stalled. The underlying needs remain.

With the failure of the bond measure and the loss of state funding, the County had little choice but to change course. Instead of pursuing a single, transformative project, it has now shifted toward a three-building strategy: 1) keep the existing courthouse; 2) expand justice‑system functions into the Public Service Building; and 3) move other operations into the Wells Fargo building.

Blocking diagram of one of the 2018 Lane County Justice Center development scenarios (Robertson/Sherwood/Architects w/DLR Group).

The Wells Fargo building is not a courthouse-ready structure. It lacks the floor-to-floor heights, structural grid, circulation patterns, and security zoning that modern courthouses require. But it can relieve pressure. By moving a mix of administrative and selected justice‑system functions into the building, including portions of the District Attorney’s Office or the Sheriff’s Office, the County frees space in the Public Service Building for the functions that most directly support the courthouse next door. The Wells Fargo building is a way to buy time and improve conditions without taking on the cost or political risk of a massive new construction project.(2)

The County says it will fund the early phases of this three‑building strategy with existing capital reserves and general‑fund allocations. These will inevitably be modest, phased investments rather than a single large capital outlay. The County will proceed without waiting for new revenue sources.

Given that funding approach, it is reasonable to ask whether selling the former City Hall block could help pay for later improvements. The short answer is yes in principle, but not in a way that changes the County’s immediate capital picture. The block holds real market value, but Eugene’s land economics remain modest. Even a full‑block sale would likely generate only a few million dollars, helpful but not transformative.

Once the County completes the Wells Fargo move, reconfigures the PSB, and outlines a long-term renovation plan for the courthouse, the narrative becomes cleaner: the block no longer serves a justice function and can return to productive private use. The most plausible scenario is that the County eventually sells or ground‑leases the block, and that the proceeds support later phases of courthouse renovation rather than the immediate work that will likely start soon.

The implications of this shift extend beyond courthouse logistics. They also reshape the civic geography of downtown Eugene. The three‑building strategy, in an unintended way, brings the County back into alignment with the city’s earliest civic geometry. When Eugene’s early trustees platted the Park Blocks in the 1850s, they imagined them as the civic heart of the town, framed by public institutions and anchored by the courthouse. That geometry has persisted for more than a century and a half. By choosing to retain the courthouse on its current site rather than construct a new facility on the former City Hall block, the County has, perhaps unwittingly, honored that original civic logic. The Park Blocks remain the symbolic center of the justice system, and the courthouse remains essentially where the founders placed the original building. With that continuity intact, the City Hall block no longer carries any inherited obligation to remain civic land.

Civic uses evolve. Land use is not a sacred inheritance. The City’s move into the former EWEB headquarters, a far better outcome than any of the City Hall schemes pursued over the past two decades, effectively freed the block from its symbolic burden. Today, the County has no program for the site, no funding to develop it, and no political narrative that would support a new civic building there. In that context, private redevelopment offers the most responsible path forward.

Google Earth view of the existing courthouse (left), Lane County Public Services Building (center), and the former City Hall block, now a parking lot owned by the County (right).

A dense mixed-use project, whether housing, hotel, retail, or office, would not reshape the Park Blocks directly. But it would repair a missing piece of the streetscape along 8th Avenue, which the City once envisioned as a “Great Street.” Today, that sequence runs from the Park Blocks to the courthouse and Public Service Building, and then simply stops. Filling the old City Hall block with active, inhabited uses would stitch the urban fabric back together. In place of a void, there could be a more continuous, coherent civic corridor. Dense mixed-use redevelopment would bring residents, visitors, and daily activity to a part of downtown that has long felt underbuilt and unresolved. In that sense, private development would strengthen the district more effectively than any modest civic use the County could plausibly afford.

Lane County’s new three‑building strategy reflects fiscal reality and political constraints. Once fully implemented, it will improve conditions for the courts, the Sheriff, and the District Attorney, even if it falls short of the comprehensive solution envisioned in 2019. The County now owes the public a clear articulation of its long-term intentions, not just for the courthouse and the Public Service Building but for the former City Hall block. Downtown Eugene deserves decisions grounded in reality rather than nostalgia. It also deserves a plan that recognizes that even modest, well-considered choices can strengthen the civic core. If the County provides that clarity, this pivot, while less ambitious than many of us once hoped for, can still move the civic district in a constructive direction.

(1) My former firm, Robertson/Sherwood/Architects, with the assistance of DLR Group’s Justice+Civic studio, prepared the study.

(2) For readers who want the underlying numbers, recent reporting in the Register‑Guard and Lookout Eugene‑Springfield covers the purchase price, building size, and early renovation estimates.