diff --git a/php/Services/BrainService.php b/php/Services/BrainService.php
index b718099..10c1593 100644
--- a/php/Services/BrainService.php
+++ b/php/Services/BrainService.php
@@ -36,6 +36,8 @@ class BrainService
 
     private const MEMORY_LOCK_WAIT_SECONDS = 5;
 
+    private const MAX_SUPERSEDE_CHAIN_DEPTH = 100;
+
     private string $qdrantApiKey;
 
     public function __construct(
@@ -125,11 +127,11 @@ class BrainService
 
         $attributes['indexed_at'] = null;
         $cleanupIds = [];
-        $supersededId = $this->normaliseMemoryId($attributes['supersedes_id'] ?? null);
-        $remember = function () use ($attributes, &$cleanupIds): BrainMemory {
-            return DB::connection('brain')->transaction(function () use ($attributes, &$cleanupIds): BrainMemory {
+        $requestedSupersededId = $this->normaliseMemoryId($attributes['supersedes_id'] ?? null);
+        $remember = function (array $rememberAttributes) use (&$cleanupIds): BrainMemory {
+            return DB::connection('brain')->transaction(function () use ($rememberAttributes, &$cleanupIds): BrainMemory {
                 $memory = new BrainMemory;
-                $memory->fill($attributes);
+                $memory->fill($rememberAttributes);
                 $memory->save();
 
                 $this->deleteSupersededMemory($memory->supersedes_id, $cleanupIds);
@@ -138,9 +140,20 @@ class BrainService
             });
         };
 
-        $memory = $supersededId !== null
-            ? $this->withMemoryIndexLock($supersededId, $remember)
-            : $remember();
+        $memory = $requestedSupersededId !== null
+            ? $this->withMemoryIndexLock($requestedSupersededId, function () use ($requestedSupersededId, $attributes, $remember): BrainMemory {
+                $resolvedSupersededId = $this->resolveSupersedeHeadId($requestedSupersededId);
+                $rememberAttributes = $attributes;
+                // Retry calls should follow the current head rather than branch from a deleted ancestor.
+                $rememberAttributes['supersedes_id'] = $resolvedSupersededId;
+
+                if ($resolvedSupersededId === $requestedSupersededId) {
+                    return $remember($rememberAttributes);
+                }
+
+                return $this->withMemoryIndexLock($resolvedSupersededId, fn (): BrainMemory => $remember($rememberAttributes));
+            })
+            : $remember($attributes);
 
         foreach ($cleanupIds as $cleanupId) {
             DeleteFromIndex::dispatch($cleanupId);
@@ -859,13 +872,59 @@ class BrainService
         $superseded = BrainMemory::query()->find($supersededId);
 
         if (! $superseded instanceof BrainMemory) {
-            return;
+            throw new \RuntimeException("Superseded memory head vanished during delete: {$supersededId}");
         }
 
         $cleanupIds[] = $superseded->id;
         $superseded->delete();
     }
 
+    private function resolveSupersedeHeadId(string $supersededId): string
+    {
+        $currentId = $supersededId;
+        $visited = [];
+        $depth = 0;
+
+        while (true) {
+            if (isset($visited[$currentId])) {
+                throw new \RuntimeException("Detected cycle while resolving supersede chain: {$supersededId}");
+            }
+
+            if ($depth >= self::MAX_SUPERSEDE_CHAIN_DEPTH) {
+                throw new \RuntimeException(
+                    "Supersede chain exceeded ".self::MAX_SUPERSEDE_CHAIN_DEPTH." hops: {$supersededId}"
+                );
+            }
+
+            $visited[$currentId] = true;
+
+            $successor = BrainMemory::withTrashed()
+                ->where('supersedes_id', $currentId)
+                ->orderByDesc('created_at')
+                ->orderByDesc('id')
+                ->first();
+
+            if ($successor instanceof BrainMemory) {
+                $currentId = $successor->id;
+                $depth++;
+
+                continue;
+            }
+
+            $current = BrainMemory::withTrashed()->find($currentId);
+
+            if (! $current instanceof BrainMemory) {
+                throw new \InvalidArgumentException("Superseded memory not found: {$supersededId}");
+            }
+
+            if ($current->trashed()) {
+                throw new \InvalidArgumentException("Superseded memory has no live head: {$supersededId}");
+            }
+
+            return $current->id;
+        }
+    }
+
     private function memoryExists(string $id): bool
     {
         return BrainMemory::query()->whereKey($id)->exists();
diff --git a/php/tests/Feature/Brain/SupersedeForgetIndexCleanupTest.php b/php/tests/Feature/Brain/SupersedeForgetIndexCleanupTest.php
index 3150d00..630fb45 100644
--- a/php/tests/Feature/Brain/SupersedeForgetIndexCleanupTest.php
+++ b/php/tests/Feature/Brain/SupersedeForgetIndexCleanupTest.php
@@ -8,6 +8,7 @@ use Core\Mod\Agentic\Jobs\DeleteFromIndex;
 use Core\Mod\Agentic\Jobs\EmbedMemory;
 use Core\Mod\Agentic\Models\BrainMemory;
 use Core\Mod\Agentic\Services\BrainService;
+use Illuminate\Support\Str;
 use Illuminate\Support\Facades\Http;
 use Illuminate\Support\Facades\Queue;
 
@@ -120,7 +121,8 @@ test('SupersedeForgetIndexCleanup_supersede_Bad_dispatches_cleanup_for_old_index
 
     expect(BrainMemory::find($oldMemory->id))->toBeNull()
         ->and(BrainMemory::withTrashed()->find($oldMemory->id)?->trashed())->toBeTrue()
-        ->and($newMemory->indexed_at)->toBeNull();
+        ->and($newMemory->indexed_at)->toBeNull()
+        ->and($newMemory->supersedes_id)->toBe($oldMemory->id);
 
     Queue::assertPushed(DeleteFromIndex::class, fn (DeleteFromIndex $job): bool => $job->memoryId === $oldMemory->id);
     Queue::assertPushed(EmbedMemory::class, fn (EmbedMemory $job): bool => $job->memoryId === $newMemory->id);
@@ -148,12 +150,111 @@ test('SupersedeForgetIndexCleanup_supersede_Ugly_dispatches_cleanup_for_never_in
 
     expect(BrainMemory::find($oldMemory->id))->toBeNull()
         ->and(BrainMemory::withTrashed()->find($oldMemory->id)?->trashed())->toBeTrue()
-        ->and($newMemory->indexed_at)->toBeNull();
+        ->and($newMemory->indexed_at)->toBeNull()
+        ->and($newMemory->supersedes_id)->toBe($oldMemory->id);
 
     Queue::assertPushed(DeleteFromIndex::class, fn (DeleteFromIndex $job): bool => $job->memoryId === $oldMemory->id);
     Queue::assertPushed(EmbedMemory::class, fn (EmbedMemory $job): bool => $job->memoryId === $newMemory->id);
 });
 
+test('SupersedeForgetIndexCleanup_supersede_Good_retries_follow_the_current_head', function (): void {
+    Queue::fake();
+    $brain = cleanupBrainService();
+    $workspace = createWorkspace();
+    $originalMemory = cleanupMemory([
+        'workspace_id' => $workspace->id,
+        'content' => 'Original memory for retry chain.',
+    ]);
+
+    $replacement = $brain->remember([
+        'workspace_id' => $workspace->id,
+        'agent_id' => 'virgil',
+        'type' => 'observation',
+        'content' => 'First replacement memory.',
+        'confidence' => 0.91,
+        'org' => 'core',
+        'project' => 'agent',
+        'supersedes_id' => $originalMemory->id,
+    ]);
+
+    $retriedReplacement = $brain->remember([
+        'workspace_id' => $workspace->id,
+        'agent_id' => 'virgil',
+        'type' => 'observation',
+        'content' => 'Retried replacement memory.',
+        'confidence' => 0.92,
+        'org' => 'core',
+        'project' => 'agent',
+        'supersedes_id' => $originalMemory->id,
+    ]);
+
+    expect($replacement->supersedes_id)->toBe($originalMemory->id)
+        ->and($retriedReplacement->supersedes_id)->toBe($replacement->id)
+        ->and(BrainMemory::find($originalMemory->id))->toBeNull()
+        ->and(BrainMemory::withTrashed()->find($originalMemory->id)?->trashed())->toBeTrue()
+        ->and(BrainMemory::find($replacement->id))->toBeNull()
+        ->and(BrainMemory::withTrashed()->find($replacement->id)?->trashed())->toBeTrue()
+        ->and(BrainMemory::find($retriedReplacement->id))->not->toBeNull();
+
+    Queue::assertPushed(DeleteFromIndex::class, 2);
+    Queue::assertPushed(DeleteFromIndex::class, fn (DeleteFromIndex $job): bool => $job->memoryId === $originalMemory->id);
+    Queue::assertPushed(DeleteFromIndex::class, fn (DeleteFromIndex $job): bool => $job->memoryId === $replacement->id);
+    Queue::assertPushed(EmbedMemory::class, 2);
+});
+
+test('SupersedeForgetIndexCleanup_supersede_Bad_throws_for_unknown_memory', function (): void {
+    Queue::fake();
+    $workspace = createWorkspace();
+    $missingMemoryId = Str::uuid()->toString();
+
+    expect(fn () => cleanupBrainService()->remember([
+        'workspace_id' => $workspace->id,
+        'agent_id' => 'virgil',
+        'type' => 'observation',
+        'content' => 'Memory with missing supersede target.',
+        'confidence' => 0.88,
+        'org' => 'core',
+        'project' => 'agent',
+        'supersedes_id' => $missingMemoryId,
+    ]))->toThrow(\InvalidArgumentException::class, "Superseded memory not found: {$missingMemoryId}");
+
+    expect(BrainMemory::count())->toBe(0);
+    Queue::assertNothingPushed();
+});
+
+test('SupersedeForgetIndexCleanup_supersede_Ugly_detects_cycles_before_writing', function (): void {
+    Queue::fake();
+    $workspace = createWorkspace();
+    $firstMemory = cleanupMemory([
+        'workspace_id' => $workspace->id,
+        'content' => 'Cycle root memory.',
+    ]);
+    $secondMemory = cleanupMemory([
+        'workspace_id' => $workspace->id,
+        'content' => 'Cycle successor memory.',
+        'supersedes_id' => $firstMemory->id,
+    ]);
+
+    $firstMemory->supersedes_id = $secondMemory->id;
+    $firstMemory->save();
+
+    expect(fn () => cleanupBrainService()->remember([
+        'workspace_id' => $workspace->id,
+        'agent_id' => 'virgil',
+        'type' => 'observation',
+        'content' => 'Memory that should fail on cycle.',
+        'confidence' => 0.9,
+        'org' => 'core',
+        'project' => 'agent',
+        'supersedes_id' => $firstMemory->id,
+    ]))->toThrow(\RuntimeException::class, "Detected cycle while resolving supersede chain: {$firstMemory->id}");
+
+    expect(BrainMemory::count())->toBe(2)
+        ->and(BrainMemory::withTrashed()->find($firstMemory->id)?->trashed())->toBeFalse()
+        ->and(BrainMemory::withTrashed()->find($secondMemory->id)?->trashed())->toBeFalse();
+    Queue::assertNothingPushed();
+});
+
 test('SupersedeForgetIndexCleanup_supersede_Ugly_skips_late_index_writes_for_deleted_memory', function (): void {
     Queue::fake();
     Http::fake();