diff --git a/packages/core/src/instruction-context.ts b/packages/core/src/instruction-context.ts
index 94d9e787ce..745ec3420c 100644
--- a/packages/core/src/instruction-context.ts
+++ b/packages/core/src/instruction-context.ts
@@ -34,6 +34,7 @@ const layer = Layer.effect(
     const source = (value: ReadonlyArray<File> | SystemContext.Unavailable) =>
       SystemContext.make({
         key,
+        description: "Ambient instructions",
         codec: Schema.toCodecJson(Files),
         load: Effect.succeed(value),
         baseline: render,
diff --git a/packages/core/src/mcp/guidance.ts b/packages/core/src/mcp/guidance.ts
index eed26170b0..b647bda4bf 100644
--- a/packages/core/src/mcp/guidance.ts
+++ b/packages/core/src/mcp/guidance.ts
@@ -31,22 +31,48 @@ const update = (previous: ReadonlyArray<Summary>, current: ReadonlyArray<Summary
     (server) => server.server,
     (before, after) => before.instructions !== after.instructions,
   )
+  const items = [
+    ...diff.added.map((server) => ({
+      key: server.server,
+      description: "MCP server instructions",
+      action: "added" as const,
+    })),
+    ...diff.removed.map((server) => ({
+      key: server.server,
+      description: "MCP server instructions",
+      action: "removed" as const,
+    })),
+    ...diff.changed.map((server) => ({
+      key: server.current.server,
+      description: "MCP server instructions",
+      action: "updated" as const,
+    })),
+  ]
   // Additions and removals render as small deltas; anything else restates the full list.
   if (diff.changed.length > 0 || (diff.added.length === 0 && diff.removed.length === 0))
-    return [
-      "The available MCP server instructions have changed. This list supersedes the previous one.",
-      render(current),
-    ].join("\n")
-  return [
-    ...(diff.added.length === 0
-      ? []
-      : ["New MCP server instructions are available in addition to those previously listed:", ...entries(diff.added)]),
-    ...(diff.removed.length === 0
-      ? []
-      : [
-          `Instructions for the following MCP servers are no longer available: ${diff.removed.map((server) => server.server).join(", ")}.`,
-        ]),
-  ].join("\n")
+    return {
+      text: [
+        "The available MCP server instructions have changed. This list supersedes the previous one.",
+        render(current),
+      ].join("\n"),
+      items,
+    }
+  return {
+    text: [
+      ...(diff.added.length === 0
+        ? []
+        : [
+            "New MCP server instructions are available in addition to those previously listed:",
+            ...entries(diff.added),
+          ]),
+      ...(diff.removed.length === 0
+        ? []
+        : [
+            `Instructions for the following MCP servers are no longer available: ${diff.removed.map((server) => server.server).join(", ")}.`,
+          ]),
+    ].join("\n"),
+    items,
+  }
 }
 
 export interface Interface {
@@ -83,6 +109,7 @@ export const layer = Layer.effect(
         if (visible.length === 0) return SystemContext.empty
         return SystemContext.make({
           key: SystemContext.Key.make("core/mcp-guidance"),
+          description: "MCP server instructions",
           codec: Schema.toCodecJson(Schema.Array(Summary)),
           load: Effect.succeed(visible),
           baseline: render,
diff --git a/packages/core/src/reference/guidance.ts b/packages/core/src/reference/guidance.ts
index 7fc4fc486c..84458cf0da 100644
--- a/packages/core/src/reference/guidance.ts
+++ b/packages/core/src/reference/guidance.ts
@@ -35,22 +35,45 @@ const update = (previous: ReadonlyArray<typeof Summary.Type>, current: ReadonlyA
     (reference) => reference.name,
     (before, after) => before.path !== after.path || before.description !== after.description,
   )
+  const items = [
+    ...diff.added.map((reference) => ({
+      key: reference.name,
+      description: reference.description ?? reference.path,
+      action: "added" as const,
+    })),
+    ...diff.removed.map((reference) => ({
+      key: reference.name,
+      description: reference.description ?? reference.path,
+      action: "removed" as const,
+    })),
+    ...diff.changed.map((reference) => ({
+      key: reference.current.name,
+      description: reference.current.description ?? reference.current.path,
+      action: "updated" as const,
+    })),
+  ]
   // Additions and removals render as small deltas; anything else restates the full list.
   if (diff.changed.length > 0 || (diff.added.length === 0 && diff.removed.length === 0))
-    return [
-      "The available project references have changed. This list supersedes the previous reference list.",
-      render(current),
-    ].join("\n")
-  return [
-    ...(diff.added.length === 0
-      ? []
-      : ["New project references are available in addition to those previously listed:", ...entries(diff.added)]),
-    ...(diff.removed.length === 0
-      ? []
-      : [
-          `The following project references are no longer available and must not be used: ${diff.removed.map((reference) => reference.name).join(", ")}.`,
-        ]),
-  ].join("\n")
+    return {
+      text: [
+        "The available project references have changed. This list supersedes the previous reference list.",
+        render(current),
+      ].join("\n"),
+      items,
+    }
+  return {
+    text: [
+      ...(diff.added.length === 0
+        ? []
+        : ["New project references are available in addition to those previously listed:", ...entries(diff.added)]),
+      ...(diff.removed.length === 0
+        ? []
+        : [
+            `The following project references are no longer available and must not be used: ${diff.removed.map((reference) => reference.name).join(", ")}.`,
+          ]),
+    ].join("\n"),
+    items,
+  }
 }
 
 export interface Interface {
@@ -77,6 +100,7 @@ const layer = Layer.effect(
         if (available.length === 0) return SystemContext.empty
         return SystemContext.make({
           key: SystemContext.Key.make("core/reference-guidance"),
+          description: "Project references",
           codec: Schema.toCodecJson(Schema.Array(Summary)),
           load: Effect.succeed(available),
           baseline: render,
diff --git a/packages/core/src/session/context-entry.ts b/packages/core/src/session/context-entry.ts
index 1f3ffdb053..5add7d3c69 100644
--- a/packages/core/src/session/context-entry.ts
+++ b/packages/core/src/session/context-entry.ts
@@ -38,6 +38,7 @@ const renderBlock = (key: Key, value: Schema.Json) =>
 const source = (entry: Info) =>
   SystemContext.make({
     key: SystemContext.Key.make(`api/${entry.key}`),
+    description: `Session context: ${entry.key}`,
     codec: Schema.toCodecJson(Schema.Json),
     load: Effect.succeed(entry.value),
     baseline: (value) => renderBlock(entry.key, value),
diff --git a/packages/core/src/skill/guidance.ts b/packages/core/src/skill/guidance.ts
index a95a1ab0b8..5ff1918e2d 100644
--- a/packages/core/src/skill/guidance.ts
+++ b/packages/core/src/skill/guidance.ts
@@ -37,22 +37,37 @@ const update = (previous: ReadonlyArray<Summary>, current: ReadonlyArray<Summary
     (skill) => skill.name,
     (before, after) => before.description !== after.description,
   )
+  const items = [
+    ...diff.added.map((skill) => ({ key: skill.name, description: skill.description, action: "added" as const })),
+    ...diff.removed.map((skill) => ({ key: skill.name, description: skill.description, action: "removed" as const })),
+    ...diff.changed.map((skill) => ({
+      key: skill.current.name,
+      description: skill.current.description,
+      action: "updated" as const,
+    })),
+  ]
   // Additions and removals render as small deltas; anything else restates the full list.
   if (diff.changed.length > 0 || (diff.added.length === 0 && diff.removed.length === 0))
-    return [
-      "The available skills have changed. This list supersedes the previous available skills list.",
-      render(current),
-    ].join("\n")
-  return [
-    ...(diff.added.length === 0
-      ? []
-      : ["New skills are available in addition to those previously listed:", ...entries(diff.added)]),
-    ...(diff.removed.length === 0
-      ? []
-      : [
-          `The following skills are no longer available and must not be used: ${diff.removed.map((skill) => skill.name).join(", ")}.`,
-        ]),
-  ].join("\n")
+    return {
+      text: [
+        "The available skills have changed. This list supersedes the previous available skills list.",
+        render(current),
+      ].join("\n"),
+      items,
+    }
+  return {
+    text: [
+      ...(diff.added.length === 0
+        ? []
+        : ["New skills are available in addition to those previously listed:", ...entries(diff.added)]),
+      ...(diff.removed.length === 0
+        ? []
+        : [
+            `The following skills are no longer available and must not be used: ${diff.removed.map((skill) => skill.name).join(", ")}.`,
+          ]),
+    ].join("\n"),
+    items,
+  }
 }
 
 export interface Interface {
@@ -82,6 +97,7 @@ const layer = Layer.effect(
           .toSorted((a, b) => a.name.localeCompare(b.name))
         return SystemContext.make({
           key: SystemContext.Key.make("core/skill-guidance"),
+          description: "Available skills",
           codec: Schema.toCodecJson(Schema.Array(Summary)),
           load: Effect.succeed(available),
           baseline: render,
diff --git a/packages/core/src/system-context/builtins.ts b/packages/core/src/system-context/builtins.ts
index 1cf470fb4a..4d481699cc 100644
--- a/packages/core/src/system-context/builtins.ts
+++ b/packages/core/src/system-context/builtins.ts
@@ -26,6 +26,7 @@ const layer = Layer.effect(
     const context = SystemContext.combine([
       SystemContext.make({
         key: SystemContext.Key.make("core/environment"),
+        description: "Environment",
         codec: Schema.toCodecJson(Schema.String),
         load: Effect.succeed(environment),
         baseline: (environment) =>
@@ -34,6 +35,7 @@ const layer = Layer.effect(
       }),
       SystemContext.make({
         key: SystemContext.Key.make("core/date"),
+        description: "Current date",
         codec: Schema.toCodecJson(Schema.String),
         load: DateTime.nowAsDate.pipe(Effect.map((date) => date.toDateString())),
         baseline: (date) => `Today's date: ${date}`,
diff --git a/packages/core/src/system-context/index.ts b/packages/core/src/system-context/index.ts
index ce6aaae454..0b486f705f 100644
--- a/packages/core/src/system-context/index.ts
+++ b/packages/core/src/system-context/index.ts
@@ -36,13 +36,34 @@ export type Unavailable = typeof unavailable
 /** Defines one typed source before its value type is hidden by `make`. */
 export interface Source<A> {
   readonly key: Key
-  readonly codec: Schema.Codec<A, Schema.Json, never, never>
+  readonly description: string
+  readonly codec: Schema.Codec<A, Schema.Json>
   readonly load: Effect.Effect<A | Unavailable>
   readonly baseline: (current: A) => string
-  readonly update: (previous: A, current: A) => string
+  readonly update: (previous: A, current: A) => string | StructuredUpdate
   readonly removed?: (previous: A) => string
 }
 
+export type ReconcileAction = "added" | "updated" | "removed"
+
+export interface ReconcileItemUpdate {
+  readonly key: string
+  readonly description: string
+  readonly action: ReconcileAction
+}
+
+export interface ReconcileUpdate {
+  readonly key: Key
+  readonly description: string
+  readonly action: ReconcileAction
+  readonly items?: ReadonlyArray<ReconcileItemUpdate>
+}
+
+export interface StructuredUpdate {
+  readonly text: string
+  readonly items?: ReadonlyArray<ReconcileItemUpdate>
+}
+
 const ContextTypeId: unique symbol = Symbol.for("@opencode/SystemContext")
 
 /** Opaque carrier for composable system context sources. */
@@ -53,6 +74,7 @@ export interface SystemContext {
 /** The value last applied to the model for one admitted source. */
 export const AppliedSource = Schema.Struct({
   value: Schema.Json,
+  description: Schema.optional(Schema.NonEmptyString),
   removed: Schema.optional(Schema.NonEmptyString),
 })
 export type AppliedSource = typeof AppliedSource.Type
@@ -70,6 +92,7 @@ export interface Baseline {
 export interface Updated {
   readonly _tag: "Updated"
   readonly text: string
+  readonly updates: ReadonlyArray<ReconcileUpdate>
   readonly applied: Applied
 }
 
@@ -94,16 +117,18 @@ export class DuplicateKeyError extends Schema.TaggedErrorClass<DuplicateKeyError
 
 interface PackedSource {
   readonly key: Key
+  readonly description: string
   readonly load: Effect.Effect<Observed | Unavailable>
   /** Restates the model's belief from a last-applied value when the source cannot be observed. */
   readonly recall: (stored: AppliedSource) => string | undefined
 }
 
 interface Observed {
+  readonly description: string
   readonly applied: AppliedSource
   readonly baseline: () => string
   /** `undefined` means unchanged. An undecodable previous value re-renders the baseline (treat-as-new). */
-  readonly update: (previous: AppliedSource) => string | undefined
+  readonly update: (previous: AppliedSource) => StructuredUpdate | undefined
 }
 
 interface Entry {
@@ -120,10 +145,12 @@ export function make<A>(source: Source<A>): SystemContext {
   const decode = Schema.decodeUnknownOption(source.codec)
   const encode = Schema.encodeSync(source.codec)
   const equivalent = Schema.toEquivalence(source.codec)
+  const description = requireText(source.key, "description", source.description)
   const baseline = (value: A) => requireText(source.key, "baseline", source.baseline(value))
   return context([
     {
       key: source.key,
+      description,
       recall: (stored) =>
         Option.match(decode(stored.value), {
           onNone: () => undefined,
@@ -133,18 +160,18 @@ export function make<A>(source: Source<A>): SystemContext {
         Effect.map((value) => {
           if (isUnavailable(value)) return value
           return {
+            description,
             applied: {
               value: encode(value),
+              description,
               ...(source.removed ? { removed: requireText(source.key, "removal", source.removed(value)) } : {}),
             },
             baseline: () => baseline(value),
             update: (previous) =>
               Option.match(decode(previous.value), {
-                onNone: () => baseline(value),
+                onNone: () => ({ text: baseline(value) }),
                 onSome: (decoded) =>
-                  equivalent(decoded, value)
-                    ? undefined
-                    : requireText(source.key, "update", source.update(decoded, value)),
+                  equivalent(decoded, value) ? undefined : normalizeUpdate(source.key, source.update(decoded, value)),
               }),
           } satisfies Observed
         }),
@@ -216,7 +243,8 @@ export function initialize(value: SystemContext): Effect.Effect<Baseline, Initia
 export function reconcile(value: SystemContext, previous: Applied): Effect.Effect<ReconcileResult> {
   return observe(value).pipe(
     Effect.map((entries): ReconcileResult => {
-      const updates: string[] = []
+      const parts: string[] = []
+      const updates: ReconcileUpdate[] = []
       const applied: Record<string, AppliedSource> = {}
       for (const entry of entries) {
         const stored = get(previous, entry.key)
@@ -226,16 +254,23 @@ export function reconcile(value: SystemContext, previous: Applied): Effect.Effec
           continue
         }
         if (!stored) {
-          updates.push(entry.observed.baseline())
+          parts.push(entry.observed.baseline())
+          updates.push({ key: entry.key, description: entry.observed.description, action: "added" })
           applied[entry.key] = entry.observed.applied
           continue
         }
-        const text = entry.observed.update(stored)
-        if (text === undefined) {
+        const update = entry.observed.update(stored)
+        if (update === undefined) {
           applied[entry.key] = stored
           continue
         }
-        updates.push(text)
+        parts.push(update.text)
+        updates.push({
+          key: entry.key,
+          description: entry.observed.description,
+          action: "updated",
+          ...(update.items === undefined ? {} : { items: update.items }),
+        })
         applied[entry.key] = entry.observed.applied
       }
       const keys = new Set<string>(entries.map((entry) => entry.key))
@@ -244,10 +279,17 @@ export function reconcile(value: SystemContext, previous: Applied): Effect.Effec
         const removed = previous[key].removed
         // An unannounced removal retains the belief; it clears at the next rebaseline.
         if (removed === undefined) applied[key] = previous[key]
-        else updates.push(removed)
+        else {
+          parts.push(removed)
+          updates.push({
+            key: Key.make(key),
+            description: previous[key].description ?? key,
+            action: "removed",
+          })
+        }
       }
       if (updates.length === 0) return { _tag: "Unchanged" }
-      return { _tag: "Updated", text: render(updates), applied }
+      return { _tag: "Updated", text: render(parts), updates, applied }
     }),
   )
 }
@@ -298,6 +340,11 @@ function requireText(key: Key, kind: string, text: string) {
   return text
 }
 
+function normalizeUpdate(key: Key, update: string | StructuredUpdate) {
+  if (typeof update === "string") return { text: requireText(key, "update", update) }
+  return { ...update, text: requireText(key, "update", update.text) }
+}
+
 function assertUniqueKeys(sources: ReadonlyArray<PackedSource>) {
   const keys = new Set<Key>()
   for (const source of sources) {
diff --git a/packages/core/test/instruction-context.test.ts b/packages/core/test/instruction-context.test.ts
index 8bd04d305a..f87dea689c 100644
--- a/packages/core/test/instruction-context.test.ts
+++ b/packages/core/test/instruction-context.test.ts
@@ -94,6 +94,13 @@ describe("InstructionContext", () => {
               `Instructions from: ${globalFile}\nglobal`,
               `Instructions from: ${projectFile}\nproject`,
             ].join("\n\n"),
+            updates: [
+              {
+                key: SystemContext.Key.make("core/instructions"),
+                description: "Ambient instructions",
+                action: "updated",
+              },
+            ],
             applied: expect.any(Object),
           })
 
@@ -101,6 +108,13 @@ describe("InstructionContext", () => {
           expect(yield* SystemContext.reconcile(yield* load, initialized.applied)).toEqual({
             _tag: "Updated",
             text: "Previously loaded instructions no longer apply.",
+            updates: [
+              {
+                key: SystemContext.Key.make("core/instructions"),
+                description: "Ambient instructions",
+                action: "removed",
+              },
+            ],
             applied: {},
           })
         }),
diff --git a/packages/core/test/session-runner.test.ts b/packages/core/test/session-runner.test.ts
index af96096266..c0420e73db 100644
--- a/packages/core/test/session-runner.test.ts
+++ b/packages/core/test/session-runner.test.ts
@@ -186,6 +186,7 @@ const systemContext = Layer.mock(SystemContextBuiltIns.Service, {
           : [
               SystemContext.make({
                 key: systemContextKey,
+                description: "Test context",
                 codec: Schema.toCodecJson(Schema.String),
                 load: systemLoadHook.pipe(
                   Effect.andThen(Effect.sync(() => (systemUnavailable ? SystemContext.unavailable : systemBaseline))),
@@ -205,6 +206,7 @@ const skillGuidance = Layer.mock(SkillGuidance.Service, {
       skillBaselines.has(agent.id)
         ? SystemContext.make({
             key: SystemContext.Key.make("test/skill-guidance"),
+            description: "Test skill guidance",
             codec: Schema.toCodecJson(Schema.String),
             load: Effect.succeed(skillBaselines.get(agent.id)!),
             baseline: String,
@@ -809,7 +811,9 @@ describe("SessionRunnerLLM", () => {
         .where(eq(SessionContextCheckpointTable.session_id, sessionID))
         .get()
         .pipe(Effect.orDie)
-      expect(healed?.snapshot).toEqual({ "test/context": { value: "Initial context", removed: expect.any(String) } })
+      expect(healed?.snapshot).toEqual({
+        "test/context": { value: "Initial context", description: "Test context", removed: expect.any(String) },
+      })
     }),
   )
 
@@ -2807,8 +2811,7 @@ describe("SessionRunnerLLM", () => {
           description: "Ask the user",
           input: Schema.Struct({}),
           output: Schema.Struct({}),
-          execute: (_, context) =>
-            questions.ask({ sessionID: context.sessionID, questions: [] }).pipe(Effect.as({}), Effect.orDie),
+          execute: (_, context) => questions.ask({ sessionID: context.sessionID, questions: [] }).pipe(Effect.as({}), Effect.orDie),
         }),
       })
       yield* session.prompt({ sessionID, prompt: Prompt.make({ text: "Ask then stop" }), resume: false })
diff --git a/packages/core/test/system-context/index.test.ts b/packages/core/test/system-context/index.test.ts
index f62053b088..c0409ce464 100644
--- a/packages/core/test/system-context/index.test.ts
+++ b/packages/core/test/system-context/index.test.ts
@@ -3,16 +3,18 @@ import { Cause, Effect, Exit, Schema } from "effect"
 import { SystemContext } from "@opencode-ai/core/system-context"
 import { it } from "../lib/effect"
 
-const key = SystemContext.Key.make
+const key = (value: string) => SystemContext.Key.make(value)
 const stringContext = (input: {
   key: string
   value: string | SystemContext.Unavailable
+  description?: string
   baseline?: (value: string) => string
-  update?: (previous: string, current: string) => string
+  update?: (previous: string, current: string) => string | SystemContext.StructuredUpdate
   removed?: (value: string) => string
 }) =>
   SystemContext.make({
     key: key(input.key),
+    description: input.description ?? `Description for ${input.key}`,
     codec: Schema.toCodecJson(Schema.String),
     load: Effect.succeed(input.value),
     baseline: input.baseline ?? String,
@@ -25,6 +27,7 @@ describe("SystemContext", () => {
     Effect.gen(function* () {
       const context = SystemContext.make({
         key: key("core/date"),
+        description: "Current date",
         codec: Schema.toCodecJson(Schema.DateFromString),
         load: Effect.succeed(new Date("2026-06-03T12:00:00.000Z")),
         baseline: (date) => date.toISOString(),
@@ -42,6 +45,7 @@ describe("SystemContext", () => {
       const context = SystemContext.combine([
         SystemContext.make({
           key: key("core/date"),
+          description: "Current date",
           codec: Schema.toCodecJson(Schema.String),
           load: Effect.sync(() => {
             loads++
@@ -57,8 +61,8 @@ describe("SystemContext", () => {
       expect(yield* SystemContext.initialize(context)).toEqual({
         text: "Today's date is 2026-06-03.\n\nDirectory: /repo",
         applied: {
-          "core/date": { value: "2026-06-03", removed: "The date was removed." },
-          "core/location": { value: "/repo" },
+          "core/date": { value: "2026-06-03", description: "Current date", removed: "The date was removed." },
+          "core/location": { value: "/repo", description: "Description for core/location" },
         },
       })
       expect(loads).toBe(1)
@@ -84,8 +88,13 @@ describe("SystemContext", () => {
       expect(yield* SystemContext.reconcile(changed, previous)).toEqual({
         _tag: "Updated",
         text: "The date changed from 2026-06-03 to 2026-06-04.",
+        updates: [{ key: key("core/date"), description: "Description for core/date", action: "updated" }],
         applied: {
-          "core/date": { value: "2026-06-04", removed: "The date was removed." },
+          "core/date": {
+            value: "2026-06-04",
+            description: "Description for core/date",
+            removed: "The date was removed.",
+          },
           "core/location": { value: "/repo", removed: "Removed: /repo" },
         },
       })
@@ -113,7 +122,8 @@ describe("SystemContext", () => {
       expect(yield* SystemContext.reconcile(context, {})).toEqual({
         _tag: "Updated",
         text: "Available skill: effect",
-        applied: { "core/skills": { value: "effect" } },
+        updates: [{ key: key("core/skills"), description: "Description for core/skills", action: "added" }],
+        applied: { "core/skills": { value: "effect", description: "Description for core/skills" } },
       })
     }),
   )
@@ -150,6 +160,7 @@ describe("SystemContext", () => {
       ).toEqual({
         _tag: "Updated",
         text: "Instructions removed; stop applying them.",
+        updates: [{ key: key("core/instructions"), description: "core/instructions", action: "removed" }],
         applied: {},
       })
     }),
@@ -169,8 +180,9 @@ describe("SystemContext", () => {
       ).toEqual({
         _tag: "Updated",
         text: "effect",
+        updates: [{ key: key("core/skills"), description: "Description for core/skills", action: "added" }],
         applied: {
-          "core/skills": { value: "effect" },
+          "core/skills": { value: "effect", description: "Description for core/skills" },
           "core/date": { value: "2026-06-04" },
         },
       })
@@ -208,7 +220,8 @@ describe("SystemContext", () => {
       ).toEqual({
         _tag: "Updated",
         text: "2026-06-04",
-        applied: { "core/date": { value: "2026-06-04" } },
+        updates: [{ key: key("core/date"), description: "Description for core/date", action: "updated" }],
+        applied: { "core/date": { value: "2026-06-04", description: "Description for core/date" } },
       })
     }),
   )
@@ -232,9 +245,13 @@ describe("SystemContext", () => {
       ).toEqual({
         _tag: "Updated",
         text: "2026-06-03 -> 2026-06-04\n\n/repo",
+        updates: [
+          { key: key("core/date"), description: "Description for core/date", action: "updated" },
+          { key: key("core/location"), description: "Description for core/location", action: "updated" },
+        ],
         applied: {
-          "core/date": { value: "2026-06-04" },
-          "core/location": { value: "/repo" },
+          "core/date": { value: "2026-06-04", description: "Description for core/date" },
+          "core/location": { value: "/repo", description: "Description for core/location" },
         },
       })
     }),
@@ -245,6 +262,7 @@ describe("SystemContext", () => {
       let loads = 0
       const context = SystemContext.make({
         key: key("core/date"),
+        description: "Current date",
         codec: Schema.toCodecJson(Schema.String),
         load: Effect.sync(() => {
           loads++
@@ -256,7 +274,7 @@ describe("SystemContext", () => {
 
       expect(yield* SystemContext.rebaseline(context, { "core/date": { value: "2026-06-03" } })).toEqual({
         text: "2026-06-04",
-        applied: { "core/date": { value: "2026-06-04" } },
+        applied: { "core/date": { value: "2026-06-04", description: "Current date" } },
       })
       expect(loads).toBe(1)
     }),
@@ -280,7 +298,7 @@ describe("SystemContext", () => {
       ).toEqual({
         text: "2026-06-04\n\nInstructions: contents",
         applied: {
-          "core/date": { value: "2026-06-04" },
+          "core/date": { value: "2026-06-04", description: "Description for core/date" },
           "core/remote": { value: "contents", removed: "Instructions removed" },
         },
       })
@@ -334,6 +352,34 @@ describe("SystemContext", () => {
     }),
   )
 
+  it.effect("includes structured item updates from source reconciliation", () =>
+    Effect.gen(function* () {
+      const context = stringContext({
+        key: "core/skills",
+        value: "new",
+        description: "Available skills",
+        update: () => ({
+          text: "Skill changes",
+          items: [{ key: "effect", description: "Build with Effect", action: "updated" }],
+        }),
+      })
+
+      expect(yield* SystemContext.reconcile(context, { "core/skills": { value: "old" } })).toEqual({
+        _tag: "Updated",
+        text: "Skill changes",
+        updates: [
+          {
+            key: key("core/skills"),
+            description: "Available skills",
+            action: "updated",
+            items: [{ key: "effect", description: "Build with Effect", action: "updated" }],
+          },
+        ],
+        applied: { "core/skills": { value: "new", description: "Available skills" } },
+      })
+    }),
+  )
+
   it.effect("rejects duplicate source keys", () =>
     Effect.sync(() => {
       expect(() =>