diff --git a/packages/core/src/mcp/guidance.ts b/packages/core/src/mcp/guidance.ts
index 89882ea19b..eed26170b0 100644
--- a/packages/core/src/mcp/guidance.ts
+++ b/packages/core/src/mcp/guidance.ts
@@ -25,28 +25,26 @@ const render = (servers: ReadonlyArray<Summary>) =>
   ["<mcp_instructions>", ...entries(servers), "</mcp_instructions>"].join("\n")
 
 const update = (previous: ReadonlyArray<Summary>, current: ReadonlyArray<Summary>) => {
-  const names = new Set(current.map((server) => server.server))
-  const previousByName = new Map(previous.map((server) => [server.server, server]))
-  const added = current.filter((server) => !previousByName.has(server.server))
-  const removed = previous.filter((server) => !names.has(server.server))
-  const changed = current.filter((server) => {
-    const before = previousByName.get(server.server)
-    return before !== undefined && before.instructions !== server.instructions
-  })
+  const diff = SystemContext.diffByKey(
+    previous,
+    current,
+    (server) => server.server,
+    (before, after) => before.instructions !== after.instructions,
+  )
   // Additions and removals render as small deltas; anything else restates the full list.
-  if (changed.length > 0 || (added.length === 0 && removed.length === 0))
+  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 [
-    ...(added.length === 0
+    ...(diff.added.length === 0
       ? []
-      : ["New MCP server instructions are available in addition to those previously listed:", ...entries(added)]),
-    ...(removed.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: ${removed.map((server) => server.server).join(", ")}.`,
+          `Instructions for the following MCP servers are no longer available: ${diff.removed.map((server) => server.server).join(", ")}.`,
         ]),
   ].join("\n")
 }
diff --git a/packages/core/src/reference/guidance.ts b/packages/core/src/reference/guidance.ts
index 6544852df2..7fc4fc486c 100644
--- a/packages/core/src/reference/guidance.ts
+++ b/packages/core/src/reference/guidance.ts
@@ -29,28 +29,26 @@ const render = (references: ReadonlyArray<typeof Summary.Type>) =>
   ].join("\n")
 
 const update = (previous: ReadonlyArray<typeof Summary.Type>, current: ReadonlyArray<typeof Summary.Type>) => {
-  const names = new Set(current.map((reference) => reference.name))
-  const previousByName = new Map(previous.map((reference) => [reference.name, reference]))
-  const added = current.filter((reference) => !previousByName.has(reference.name))
-  const removed = previous.filter((reference) => !names.has(reference.name))
-  const changed = current.filter((reference) => {
-    const before = previousByName.get(reference.name)
-    return before !== undefined && (before.path !== reference.path || before.description !== reference.description)
-  })
+  const diff = SystemContext.diffByKey(
+    previous,
+    current,
+    (reference) => reference.name,
+    (before, after) => before.path !== after.path || before.description !== after.description,
+  )
   // Additions and removals render as small deltas; anything else restates the full list.
-  if (changed.length > 0 || (added.length === 0 && removed.length === 0))
+  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 [
-    ...(added.length === 0
+    ...(diff.added.length === 0
       ? []
-      : ["New project references are available in addition to those previously listed:", ...entries(added)]),
-    ...(removed.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: ${removed.map((reference) => reference.name).join(", ")}.`,
+          `The following project references are no longer available and must not be used: ${diff.removed.map((reference) => reference.name).join(", ")}.`,
         ]),
   ].join("\n")
 }
diff --git a/packages/core/src/skill/guidance.ts b/packages/core/src/skill/guidance.ts
index abca17b6b0..a95a1ab0b8 100644
--- a/packages/core/src/skill/guidance.ts
+++ b/packages/core/src/skill/guidance.ts
@@ -31,28 +31,26 @@ const render = (skills: ReadonlyArray<Summary>) =>
   ].join("\n")
 
 const update = (previous: ReadonlyArray<Summary>, current: ReadonlyArray<Summary>) => {
-  const names = new Set(current.map((skill) => skill.name))
-  const previousByName = new Map(previous.map((skill) => [skill.name, skill]))
-  const added = current.filter((skill) => !previousByName.has(skill.name))
-  const removed = previous.filter((skill) => !names.has(skill.name))
-  const changed = current.filter((skill) => {
-    const before = previousByName.get(skill.name)
-    return before !== undefined && before.description !== skill.description
-  })
+  const diff = SystemContext.diffByKey(
+    previous,
+    current,
+    (skill) => skill.name,
+    (before, after) => before.description !== after.description,
+  )
   // Additions and removals render as small deltas; anything else restates the full list.
-  if (changed.length > 0 || (added.length === 0 && removed.length === 0))
+  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 [
-    ...(added.length === 0
+    ...(diff.added.length === 0
       ? []
-      : ["New skills are available in addition to those previously listed:", ...entries(added)]),
-    ...(removed.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: ${removed.map((skill) => skill.name).join(", ")}.`,
+          `The following skills are no longer available and must not be used: ${diff.removed.map((skill) => skill.name).join(", ")}.`,
         ]),
   ].join("\n")
 }
diff --git a/packages/core/src/system-context/index.ts b/packages/core/src/system-context/index.ts
index e9b04cb480..ce6aaae454 100644
--- a/packages/core/src/system-context/index.ts
+++ b/packages/core/src/system-context/index.ts
@@ -153,6 +153,32 @@ export function make<A>(source: Source<A>): SystemContext {
   ])
 }
 
+/**
+ * Keyed three-way diff for list-shaped sources rendering delta updates.
+ * `changed` compares two values sharing a key; entries equal under it are dropped.
+ */
+export function diffByKey<A>(
+  previous: ReadonlyArray<A>,
+  current: ReadonlyArray<A>,
+  key: (value: A) => string,
+  changed: (previous: A, current: A) => boolean,
+): {
+  readonly added: ReadonlyArray<A>
+  readonly removed: ReadonlyArray<A>
+  readonly changed: ReadonlyArray<{ readonly previous: A; readonly current: A }>
+} {
+  const currentKeys = new Set(current.map(key))
+  const previousByKey = new Map(previous.map((value) => [key(value), value] as const))
+  return {
+    added: current.filter((value) => !previousByKey.has(key(value))),
+    removed: previous.filter((value) => !currentKeys.has(key(value))),
+    changed: current.flatMap((value) => {
+      const before = previousByKey.get(key(value))
+      return before === undefined || !changed(before, value) ? [] : [{ previous: before, current: value }]
+    }),
+  }
+}
+
 /** Combines contexts in order and rejects duplicate source keys immediately. */
 export function combine(values: ReadonlyArray<SystemContext>): SystemContext {
   const sources = values.flatMap((value) => value[ContextTypeId])
diff --git a/packages/core/test/system-context/index.test.ts b/packages/core/test/system-context/index.test.ts
index 492829c34d..f62053b088 100644
--- a/packages/core/test/system-context/index.test.ts
+++ b/packages/core/test/system-context/index.test.ts
@@ -301,6 +301,39 @@ describe("SystemContext", () => {
     }),
   )
 
+  it.effect("diffs list values by key with a changed comparator", () =>
+    Effect.sync(() => {
+      const previous = [
+        { name: "effect", description: "Build with Effect" },
+        { name: "debugging", description: "Diagnose bugs" },
+        { name: "retired", description: "Old" },
+      ]
+      const current = [
+        { name: "effect", description: "Build with Effect v4" },
+        { name: "debugging", description: "Diagnose bugs" },
+        { name: "writing", description: "Write prose" },
+      ]
+
+      expect(
+        SystemContext.diffByKey(
+          previous,
+          current,
+          (value) => value.name,
+          (before, after) => before.description !== after.description,
+        ),
+      ).toEqual({
+        added: [{ name: "writing", description: "Write prose" }],
+        removed: [{ name: "retired", description: "Old" }],
+        changed: [
+          {
+            previous: { name: "effect", description: "Build with Effect" },
+            current: { name: "effect", description: "Build with Effect v4" },
+          },
+        ],
+      })
+    }),
+  )
+
   it.effect("rejects duplicate source keys", () =>
     Effect.sync(() => {
       expect(() =>