From 7f40224f0f6c908e31108252f66816b6cd0b57a1 Mon Sep 17 00:00:00 2001
From: John Dvorak <john@johnsdvorak.com>
Date: Fri, 22 May 2026 13:46:54 -0700
Subject: [PATCH] fix: propagate compound state through toAst() and canonical
 lowering

ast.ts: Add optional compoundOperator and compoundParts fields to
  RelationAssertion, allowing compound fluent assertions to carry
  their .and / .or structure through the AST layer.

fluent.ts: toAst() now emits compoundOperator/compoundParts when
  isCompound, closing the gap where compound state was silently
  dropped in canonical extraction, preset building, and validation.

lower-to-canonical.ts: Handle RelationAssertion with compound metadata
  by lowering each part as a separate grouped clause (same groupId,
  same compoundOperator), matching DSL parser compound behavior.

validator.ts: Validate options on each compound part, closing the
  false-positive validation gap where only the final relation was checked.

3 lossy code paths (extractCanonicalFromAssertion, presets.toPresetResult,
validateRelation) now preserve compound structure. Primary FOL evaluation
path was already correct (fol-compiler reads compoundParts directly).

658 tests pass.
---
 packages/imhotep-core/src/ast.ts              |  4 ++++
 packages/imhotep-dsl/src/fluent.ts            | 10 +++++++++
 .../imhotep-dsl/src/lower-to-canonical.ts     | 19 +++++++++++++++-
 packages/imhotep-dsl/src/validator.ts         | 22 +++++++++++++++++++
 4 files changed, 54 insertions(+), 1 deletion(-)

diff --git a/packages/imhotep-core/src/ast.ts b/packages/imhotep-core/src/ast.ts
index b6d5575..d3885f0 100644
--- a/packages/imhotep-core/src/ast.ts
+++ b/packages/imhotep-core/src/ast.ts
@@ -110,6 +110,10 @@ export interface RelationAssertion extends AstNode {
   subject: SelectorRef
   reference: SelectorRef
   options: RelationOptions
+  /** If set, this assertion is part of a compound (.and / .or) chain. */
+  compoundOperator?: 'and' | 'or'
+  /** Sub-relation parts forming the compound chain (including this one). */
+  compoundParts?: Array<{ relation: string; referenceSelector: string; options: RelationOptions }>
 }
 
 export interface RelationOptions extends AstNode {
diff --git a/packages/imhotep-dsl/src/fluent.ts b/packages/imhotep-dsl/src/fluent.ts
index e6c54ff..3837c99 100644
--- a/packages/imhotep-dsl/src/fluent.ts
+++ b/packages/imhotep-dsl/src/fluent.ts
@@ -783,6 +783,16 @@ export class FluentRelation {
       opts.space = space
     }
 
+    // Emit compound metadata so canonical lowering preserves .and / .or chains
+    if (this.isCompound) {
+      base.compoundOperator = this._compoundOperator
+      base.compoundParts = this._compoundParts.map(p => ({
+        relation: p.relation,
+        referenceSelector: p.referenceSelector,
+        options: p.options as unknown as import('imhotep-core').RelationOptions,
+      }))
+    }
+
     return base
   }
 }
diff --git a/packages/imhotep-dsl/src/lower-to-canonical.ts b/packages/imhotep-dsl/src/lower-to-canonical.ts
index ac280e7..8987ce3 100644
--- a/packages/imhotep-dsl/src/lower-to-canonical.ts
+++ b/packages/imhotep-dsl/src/lower-to-canonical.ts
@@ -156,7 +156,24 @@ export function lowerToCanonical(ast: RelationAssertion | Program): CanonicalCla
       lowerBlock(child as any, descriptors, {}, undefined, () => { compoundGroupId += 1; return compoundGroupId })
     }
   } else {
-    descriptors.push(lowerAssertionToCanonical(ast, {}))
+    // Check for compound metadata on a RelationAssertion (from fluent API toAst())
+    const rel = ast as RelationAssertion
+    if (rel.type === 'RelationAssertion' && rel.compoundOperator && rel.compoundParts && rel.compoundParts.length > 1) {
+      // Lower each part as a separate clause with the same compound group ID
+      const groupId = compoundGroupId += 1
+      for (const part of rel.compoundParts) {
+        const partAst: RelationAssertion = { ...rel, relation: part.relation, options: part.options }
+        if (part.referenceSelector) {
+          partAst.reference = { ...rel.reference, value: part.referenceSelector }
+        }
+        const desc = lowerAssertionToCanonical(partAst, {})
+        desc.compoundOperator = rel.compoundOperator
+        desc.compoundGroupId = groupId
+        descriptors.push(desc)
+      }
+    } else {
+      descriptors.push(lowerAssertionToCanonical(ast, {}))
+    }
   }
 
   return descriptors
diff --git a/packages/imhotep-dsl/src/validator.ts b/packages/imhotep-dsl/src/validator.ts
index 44274d5..f41b8ef 100644
--- a/packages/imhotep-dsl/src/validator.ts
+++ b/packages/imhotep-dsl/src/validator.ts
@@ -262,6 +262,28 @@ export function validateRelation(assertion: RelationAssertion): ValidationResult
     )
   }
 
+  // 6. Compound parts: validate each part's relation name and options
+  if (assertion.compoundOperator && assertion.compoundParts && assertion.compoundParts.length > 1) {
+    for (let i = 0; i < assertion.compoundParts.length; i++) {
+      const part = assertion.compoundParts[i]
+      const partAllowed = getValidOptionsForRelation(part.relation)
+      const partOpts = part.options as unknown as Record<string, unknown>
+      const partProvided = Object.keys(partOpts).filter(k => k !== 'type')
+      for (const key of partProvided) {
+        if (!partAllowed.has(key)) {
+          diagnostics.push(
+            makeDiag(
+              'IMH_VALID_ILLEGAL_RELATION_OPTION',
+              'validation-error',
+              `Option "${key}" is not valid for compound part "${part.relation}". Allowed options: ${Array.from(partAllowed).join(', ') || 'none'}.`,
+              assertion.position,
+            ),
+          )
+        }
+      }
+    }
+  }
+
   return {
     valid: diagnostics.length === 0,
     diagnostics,