diff --git a/standalone/src/jvmMain/kotlin/pw/binom/agentik/standalone/agent/ChatAgent.kt b/standalone/src/jvmMain/kotlin/pw/binom/agentik/standalone/agent/ChatAgent.kt
index 1f5f51d..0dfc3a6 100644
--- a/standalone/src/jvmMain/kotlin/pw/binom/agentik/standalone/agent/ChatAgent.kt
+++ b/standalone/src/jvmMain/kotlin/pw/binom/agentik/standalone/agent/ChatAgent.kt
@@ -212,11 +212,6 @@ class ChatAgent(
         if (!temp) {
             runBlocking {
                 storage.conversationStore.upsert(rec)
-                storage.workingMemoryStore.append(
-                    conversationId = id,
-                    entry = WorkingMemoryEntry.System(text = systemPrompt),
-                    now = now,
-                )
             }
         }
         val conv = ChatConversation(
diff --git a/standalone/src/jvmMain/kotlin/pw/binom/agentik/standalone/agent/ChatConversation.kt b/standalone/src/jvmMain/kotlin/pw/binom/agentik/standalone/agent/ChatConversation.kt
index 816c2cb..3985cac 100644
--- a/standalone/src/jvmMain/kotlin/pw/binom/agentik/standalone/agent/ChatConversation.kt
+++ b/standalone/src/jvmMain/kotlin/pw/binom/agentik/standalone/agent/ChatConversation.kt
@@ -473,12 +473,12 @@ class ChatConversation(
     private suspend fun compactPreTurn(force: Boolean): Boolean {
         val window = contextWindow ?: return false
         val compactor = contextCompactor ?: return false
+        // System prompt живёт только in-memory в ChatConversation.systemPrompt —
+        // он не участвует ни в working_memory, ни в compaction.
         val wm = workingMemory.list(id)
         if (wm.isEmpty()) return false
 
-        val systemText = wm.firstOrNull { it.entry is WorkingMemoryEntry.System }
-            ?.let { (it.entry as WorkingMemoryEntry.System).text }
-            ?: systemPrompt
+        val systemText = systemPrompt
         val history = wm.filter { it.entry is WorkingMemoryEntry.User || it.entry is WorkingMemoryEntry.Assistant }
         val toolsChars = tools.sumOf { it.tool.describe().length }
 
@@ -854,13 +854,14 @@ class ChatConversation(
     private suspend fun getOrCreateLiteConversation(excludeUserSourceId: String? = null): LiteConversation {
         liteConv?.let { return it }
 
-        val wm = if (record.isTemporal) emptyList() else workingMemory.list(id)
-        val resolvedSystemPrompt = if (record.isTemporal) systemPrompt else wm
-            .firstOrNull { it.entry is WorkingMemoryEntry.System }
-            ?.let { (it.entry as WorkingMemoryEntry.System).text }
-            ?: systemPrompt
-
-        val pastTurns: List<LiteMessage> = if (record.isTemporal) emptyList() else wm
+        // System prompt передаётся в LiteConversationConfig.systemInstruction, не в
+        // initialMessages. Хранится ТОЛЬКО in-memory в ChatConversation.systemPrompt,
+        // при каждом создании LiteConversation берётся свежий (отражает текущий SOUL,
+        // активные toolsets, актуальные skills/reflections на момент старта ChatAgent).
+        // В working_memory System-entries не пишем — иначе старые диалоги видели бы
+        // замороженный на момент создания промпт, и SOUL/toolsets не обновлялись бы
+        // без рестарта агента.
+        val pastTurns: List<LiteMessage> = if (record.isTemporal) emptyList() else workingMemory.list(id)
             .filter { row ->
                 val isUserOrAssistant = row.entry is WorkingMemoryEntry.User || row.entry is WorkingMemoryEntry.Assistant
                 val isPendingUser = excludeUserSourceId != null && row.sourceMessageId == excludeUserSourceId
@@ -880,7 +881,7 @@ class ChatConversation(
             }
 
         val config = LiteConversationConfig(
-            systemInstruction = resolvedSystemPrompt.takeIf { it.isNotBlank() },
+            systemInstruction = systemPrompt.takeIf { it.isNotBlank() },
             initialMessages = pastTurns,
             tools = tools.map { it.tool },
         )
diff --git a/standalone/src/jvmTest/kotlin/pw/binom/agentik/standalone/agent/ChatAgentTest.kt b/standalone/src/jvmTest/kotlin/pw/binom/agentik/standalone/agent/ChatAgentTest.kt
index cd31502..e3e7fd2 100644
--- a/standalone/src/jvmTest/kotlin/pw/binom/agentik/standalone/agent/ChatAgentTest.kt
+++ b/standalone/src/jvmTest/kotlin/pw/binom/agentik/standalone/agent/ChatAgentTest.kt
@@ -71,32 +71,41 @@ class ChatAgentTest {
     )
 
     @Test
-    fun `createConversation seeds system prompt into working memory`() = runTest {
+    fun `createConversation does NOT seed system prompt into working memory`() = runTest {
+        // System prompt живёт ТОЛЬКО in-memory в ChatConversation.systemPrompt
+        // и едет в LLM через LiteConversationConfig.systemInstruction. В
+        // working_memory ничего не пишется — старт system prompt чистый,
+        // 0 entries.
         val agent = newAgent()
         val conv = agent.createConversation(temp = false) as ChatConversation
 
         val wm = storage.workingMemoryStore.list(conv.id)
-        assertEquals(1, wm.size)
-        val first = wm[0]
-        val sysEntry = first.entry as pw.binom.agentik.storage.WorkingMemoryEntry.System
-        assertEquals("be brief", sysEntry.text)
+        assertEquals(0, wm.size)
+        // System prompt виден через LiteConversationConfig, который LLM получит
+        // при первом send (см. `send passes system prompt and past history to LLM on first send`).
     }
 
     @Test
-    fun `skills are appended to the system prompt in working memory`() = runTest {
+    fun `skills are appended to the system prompt passed to LLM`() = runTest {
+        // Skills добавляются в system prompt на лету при сборке ChatAgent.
+        // Проверяем это через то, что увидит LLM — systemInstruction в
+        // LiteConversationConfig (а не через working_memory, куда теперь
+        // ничего про system prompt не пишется).
         val skills = SkillCatalog(
             listOf(SkillFile(name = "lint", description = "lint things", body = "SECRET BODY")),
         )
         val agent = newAgent(skills = skills)
-        val conv = agent.createConversation(temp = false) as ChatConversation
+        val conv = agent.createConversation(temp = false)
+        fakeLlm.reply = "ok"
+        conv.send(listOf(Content.Text("hi")))
 
-        val system = storage.workingMemoryStore.list(conv.id).first().entry
-                as pw.binom.agentik.storage.WorkingMemoryEntry.System
-        assertTrue("be brief" in system.text)
-        assertTrue("## Навыки" in system.text)
-        assertTrue("lint" in system.text)
-        assertTrue("lint things" in system.text)
-        assertFalse("SECRET BODY" in system.text, "system prompt must not leak the skill body")
+        val system = fakeLlm.lastConfig!!.systemInstruction
+        assertNotNull(system)
+        assertTrue("be brief" in system!!, "base prompt missing: $system")
+        assertTrue("## Навыки" in system, "skills section missing: $system")
+        assertTrue("lint" in system, "skill name missing: $system")
+        assertTrue("lint things" in system, "skill description missing: $system")
+        assertFalse("SECRET BODY" in system, "system prompt must not leak the skill body")
     }
 
     @Test
@@ -199,12 +208,13 @@ class ChatAgentTest {
         fakeLlm.reply = "second reply"
         conv2.send(listOf(Content.Text("second user")))
 
-        // Первая беседа должна иметь только свою систему + 1 user + 1 assistant
+        // В working_memory теперь НЕТ System-entries — только user + assistant.
+        // Системный промт живёт в ChatConversation.systemPrompt и едет в LLM
+        // через LiteConversationConfig.systemInstruction.
         val wm1 = storage.workingMemoryStore.list(conv1.id)
-        assertEquals(3, wm1.size)
-        // Вторая беседа — только своё
+        assertEquals(2, wm1.size)
         val wm2 = storage.workingMemoryStore.list(conv2.id)
-        assertEquals(3, wm2.size)
+        assertEquals(2, wm2.size)
     }
 
     @Test
@@ -236,14 +246,14 @@ class ChatAgentTest {
 
         fakeLlm.reply = "first reply"
         conv.send(listOf(Content.Text("first user")))
-        // первый turn: WM = [system, user, assistant]
-        assertEquals(3, storage.workingMemoryStore.list(conv.id).size)
+        // первый turn: WM = [user, assistant] (system prompt не пишется в WM)
+        assertEquals(2, storage.workingMemoryStore.list(conv.id).size)
 
         fakeLlm.reply = "second reply"
         conv.send(listOf(Content.Text("second user")))
-        // второй turn: WM должен вырасти до [system, user, assistant, user, assistant]
+        // второй turn: WM должен вырасти до [user, assistant, user, assistant]
         val wm = storage.workingMemoryStore.list(conv.id)
-        assertEquals(5, wm.size)
+        assertEquals(4, wm.size)
         // Длинно-живущий LiteConversation: один на ChatConversation, история
         // накапливается через sendStreamContents, без пересоздания.
         assertEquals(1, fakeLlm.conversations.size)
diff --git a/standalone/src/jvmTest/kotlin/pw/binom/agentik/standalone/agent/MemoryWiringTest.kt b/standalone/src/jvmTest/kotlin/pw/binom/agentik/standalone/agent/MemoryWiringTest.kt
index e19988c..5c30dd1 100644
--- a/standalone/src/jvmTest/kotlin/pw/binom/agentik/standalone/agent/MemoryWiringTest.kt
+++ b/standalone/src/jvmTest/kotlin/pw/binom/agentik/standalone/agent/MemoryWiringTest.kt
@@ -29,7 +29,6 @@ import pw.binom.agentik.standalone.agent.memory.MemoryToolsFactory
 import pw.binom.agentik.standalone.llm.LlmBackend
 import pw.binom.agentik.standalone.llm.LlmConfig
 import pw.binom.agentik.standalone.llm.OpenAiConfig
-import pw.binom.agentik.storage.WorkingMemoryEntry
 import pw.binom.agentik.storage.sqlite.SqliteStores
 import kotlin.test.AfterTest
 import kotlin.test.BeforeTest
@@ -88,11 +87,13 @@ class MemoryWiringTest {
         val system = openMdMemorySystem(root)
         val agent = newAgent(system.store, system.prefetcher, system.reviewer)
         val conv = agent.createConversation(temp = false)
-        val wm = storage.workingMemoryStore.list(conv.id)
-        val sysRow = wm.first { it.entry is WorkingMemoryEntry.System }
-        val text = (sysRow.entry as WorkingMemoryEntry.System).text
-        assertTrue(text.contains(MemorySystemGuidance.MEMORY_GUIDANCE.take(80)),
-            "system prompt should contain MEMORY_GUIDANCE")
+        fakeLlm.reply = "ok"
+        conv.send(listOf(Content.Text("hi")))
+        // System prompt не пишется в working_memory — читаем то, что увидит LLM
+        val text = fakeLlm.lastConfig?.systemInstruction
+        assertNotNull(text)
+        assertTrue(text!!.contains(MemorySystemGuidance.MEMORY_GUIDANCE.take(80)),
+            "system prompt should contain MEMORY_GUIDANCE; got first 200 chars: ${text.take(200)}")
         agent.close()
         system.close()
     }
@@ -112,10 +113,11 @@ class MemoryWiringTest {
             soulBody = soulBody,
         )
         val conv = agent.createConversation(temp = false)
-        val wm = storage.workingMemoryStore.list(conv.id)
-        val sysRow = wm.first { it.entry is WorkingMemoryEntry.System }
-        val text = (sysRow.entry as WorkingMemoryEntry.System).text
-        assertTrue(text.startsWith(soulBody),
+        fakeLlm.reply = "ok"
+        conv.send(listOf(Content.Text("hi")))
+        val text = fakeLlm.lastConfig?.systemInstruction
+        assertNotNull(text)
+        assertTrue(text!!.startsWith(soulBody),
             "soul should be the very first section; got first 60 chars: ${text.take(60)}")
         assertTrue(text.contains("be brief"),
             "base prompt should still follow the soul; got: $text")
@@ -135,10 +137,11 @@ class MemoryWiringTest {
             ),
         )
         val conv = agent.createConversation(temp = false)
-        val wm = storage.workingMemoryStore.list(conv.id)
-        val sysRow = wm.first { it.entry is WorkingMemoryEntry.System }
-        val text = (sysRow.entry as WorkingMemoryEntry.System).text
-        assertTrue(text.startsWith("be brief"),
+        fakeLlm.reply = "ok"
+        conv.send(listOf(Content.Text("hi")))
+        val text = fakeLlm.lastConfig?.systemInstruction
+        assertNotNull(text)
+        assertTrue(text!!.startsWith("be brief"),
             "without soul, prompt should start with base; got first 60 chars: ${text.take(60)}")
         agent.close()
     }