diff --git a/docs/testing.md b/docs/testing.md
index f8a2091..fd9e467 100644
--- a/docs/testing.md
+++ b/docs/testing.md
@@ -22,17 +22,22 @@
 │   │   ├── test_events.py         # 17 tests
 │   │   ├── test_context_builder.py
 │   │   ├── test_compressor.py
-│   │   ├── test_registry.py
+│   │   ├── test_registry.py       # registries, backend discovery, context provider registry
 │   │   ├── test_planning.py
 │   │   ├── test_agent_context_size.py
 │   │   └── test_agent_stream_guard.py
+│   ├── llm/
+│   │   └── test_ollama.py         # timeout/error classification + fallback timeout wiring
 │   ├── memory/
 │   │   ├── test_store.py
 │   │   └── test_extractor.py
 │   ├── tools/
 │   │   ├── test_filesystem.py
 │   │   ├── test_code_exec.py
-│   │   └── test_terminal.py
+│   │   ├── test_terminal.py
+│   │   ├── test_share_file.py
+│   │   └── test_content_publish.py
+│   └── test_content_store.py
 │   ├── profiles/
 │   │   └── test_base.py
 │   └── config/
@@ -90,7 +95,7 @@
 |-------|--------|-------|--------|
 | 1 | `navi.core.events` | 17 | ✅ Done |
 | 1 | `navi.core.compressor` | 14 | ✅ Done |
-| 1 | `navi.core.registry` | 10 | ✅ Done |
+| 1 | `navi.core.registry` + `ContextProviderRegistry` | 13 | ✅ Done |
 | 1 | `navi.core.context_builder` | 9 | ✅ Done |
 | 1 | `navi.profiles.base` | 9 | ✅ Done |
 | 2 | `navi.memory.store` | 18 | ✅ Done |
@@ -102,12 +107,82 @@
 | 5 | `navi.tools.filesystem` | 13 | ✅ Done |
 | 5 | `navi.tools.code_exec` | 5 | ✅ Done |
 | 5 | `navi.tools.terminal` | 4 | ✅ Done |
+| 5 | `navi.tools.share_file` | 4 | ✅ Basic |
+| 5 | `navi.tools.content_publish` | 4 | ✅ Basic |
+| 5 | `navi.content_store` | 3 | ✅ Basic |
+| 5 | `navi.llm.ollama` + fallback timeout wiring | 3 | ✅ Basic |
 | 6 | `webclient/api` | 8 | ✅ Done |
 | 6 | `webclient/stores/chat` | 23 | ✅ Done |
 | 6 | `webclient/stores/sessions` | 6 | ✅ Done |
 | 6 | `webclient/stores/profiles` | 3 | ✅ Done |
 | 6 | `webclient/composables/useWebSocket` | 7 | ✅ Done |
 
+## Coverage roadmap
+
+This is the living plan for what still needs tests. Keep it updated whenever a
+bug is fixed, a new module is added, or a planned area becomes covered.
+
+Status meanings:
+- ✅ Covered enough for current risk
+- 🟨 Basic coverage exists, important edge cases remain
+- ⬜ Not covered yet
+- 🔴 Regression target from a real bug
+
+### Phase 7 — Recent Regression Coverage
+
+| Priority | Area | Target tests | Status |
+|---|---|---|---|
+| P0 | `navi.content_store.ensure_tables()` | creates `session_content`, creates `idx_session_content_file`, is idempotent when index already exists | 🟨 |
+| P0 | `navi.content_store.publish()` | repeated publish of same `(session_id, filename)` updates one row instead of creating duplicates | 🟨 🔴 |
+| P0 | `navi.main` startup | registries are initialized before `_check_embed()` so memory has an embedding backend | ⬜ 🔴 |
+| P0 | `navi.core.registry._discover_backends()` | primary Ollama backend receives HTTP timeout >= `LLM_COMPLETE_TIMEOUT` and `LLM_STREAM_FIRST_CHUNK_TIMEOUT` | ✅ 🔴 |
+| P0 | `navi.llm.fallback.FallbackOllamaBackend` | per-server `OllamaBackend` clients receive the same expanded timeout | ✅ 🔴 |
+| P1 | `navi.tools.content_publish` | missing file, directory instead of file, successful publish metadata, filename path stripping | ✅ |
+| P1 | `navi.tools.share_file` | duplicate filename collision produces numbered output without overwrite | ⬜ |
+| P1 | `navi.api.routes.sessions` file endpoints | upload duplicate naming, forbidden extension, download path traversal, content disposition | 🟨 |
+
+### Phase 8 — Agent Loop Behavior
+
+| Priority | Area | Target tests | Status |
+|---|---|---|---|
+| P0 | `Agent.run_stream()` planning entry | first user message forces planning; later messages follow `planning_enabled` | ⬜ |
+| P0 | plan → todo bridge | numbered plan steps auto-populate todo exactly once per plan | ⬜ |
+| P0 | stop handling | stop during stream prefill yields `StreamStopped` and closes LLM generator | 🟨 |
+| P1 | subagent forwarding | parent forwards subagent tool events and counts subagent tokens/tool calls | ⬜ |
+| P1 | adaptive replan | newly failed todo step injects replan prompt on next iteration | ⬜ |
+| P1 | anti-stall | repeated tool calls or no todo progress inject warning after threshold | ⬜ |
+| P1 | workers | post-turn workers run after `StreamEnd`; worker failure is logged and non-fatal | ⬜ |
+
+### Phase 9 — Memory And Embeddings
+
+| Priority | Area | Target tests | Status |
+|---|---|---|---|
+| P0 | embedding backend wiring | `get_registries()` wires dedicated `EMBEDDING_OLLAMA_HOST` backend into `MemoryStore` | ⬜ |
+| P0 | pgvector detection | `_has_pgvector()` true/false paths and caching behavior | ⬜ |
+| P1 | embedding generation | invalid/empty/NaN vectors are skipped before PostgreSQL update | 🟨 |
+| P1 | backfill | `backfill_embeddings()` batches rows and only updates rows with valid vectors | 🟨 |
+| P1 | search | vector search falls back to ILIKE when vector search unavailable or empty | 🟨 |
+
+### Phase 10 — WebSocket And API Lifecycles
+
+| Priority | Area | Target tests | Status |
+|---|---|---|---|
+| P0 | active run guard | duplicate message while a run is active returns `run_already_active` | 🟨 |
+| P0 | reconnect replay | reconnect receives missed events and session sync after finished run | 🟨 |
+| P1 | stop endpoint | `POST /sessions/{id}/stop` sets stop event and is idempotent | 🟨 |
+| P1 | malformed input | oversize images, invalid file refs, and non-string payloads are rejected or sanitized | ⬜ |
+| P1 | startup cleanup | session file cleanup task is started once and deletes orphaned dirs | ⬜ |
+
+### Phase 11 — Frontend
+
+| Priority | Area | Target tests | Status |
+|---|---|---|---|
+| P0 | `ContentCard.vue` | renders download links and inline viewer links; handles encoded filenames | ⬜ |
+| P0 | streaming chat | auto-scroll and streaming message updates stay reactive | 🟨 |
+| P1 | session switching | concurrent session loads cannot overwrite active session with stale response | 🟨 |
+| P1 | error surfaces | API/store failures show recoverable UI state, no unhandled rejection | 🟨 |
+| P1 | file upload UI | upload success/failure, duplicate names, large-file errors | ⬜ |
+
 ## Running tests
 
 ```bash
diff --git a/navi/context_providers/_loader.py b/navi/context_providers/_loader.py
index e5e67c1..03f53b3 100644
--- a/navi/context_providers/_loader.py
+++ b/navi/context_providers/_loader.py
@@ -45,6 +45,9 @@
     def all_names(self) -> list[str]:
         return list(self._providers)
 
+    def all(self) -> list[Any]:
+        return list(self._providers.values())
+
     def get_globals(self) -> list[Any]:
         return [p for p in self._providers.values() if getattr(p, "global_provider", False)]
 
diff --git a/navi/core/registry.py b/navi/core/registry.py
index 4cb3940..99f6820 100644
--- a/navi/core/registry.py
+++ b/navi/core/registry.py
@@ -116,6 +116,11 @@
     from navi.llm.ollama import OllamaBackend
     from navi.llm.fallback import FallbackOllamaBackend
     from navi.llm.openai_backend import OpenAIBackend
+    ollama_http_timeout = max(
+        settings.ollama_request_timeout,
+        settings.llm_complete_timeout,
+        settings.llm_stream_first_chunk_timeout,
+    )
 
     # Ollama backend (primary)
     if settings.ollama_backends_file:
@@ -126,6 +131,7 @@
             model=settings.ollama_default_model,
             host=settings.ollama_host,
             api_key=settings.ollama_api_key,
+            timeout=ollama_http_timeout,
         )))
 
     # OpenAI backend (if configured)
diff --git a/navi/llm/fallback.py b/navi/llm/fallback.py
index 163d87f..9bb8106 100644
--- a/navi/llm/fallback.py
+++ b/navi/llm/fallback.py
@@ -79,9 +79,14 @@
     def _get_client(self, server: ServerEntry) -> OllamaBackend:
         from navi.config import settings
         if server.host not in self._clients:
+            ollama_http_timeout = max(
+                settings.ollama_request_timeout,
+                settings.llm_complete_timeout,
+                settings.llm_stream_first_chunk_timeout,
+            )
             self._clients[server.host] = OllamaBackend(
                 model="", host=server.host, api_key=server.api_key,
-                timeout=settings.ollama_request_timeout,
+                timeout=ollama_http_timeout,
             )
         return self._clients[server.host]
 
diff --git a/navi/llm/ollama.py b/navi/llm/ollama.py
index aa5db4c..5e0146c 100644
--- a/navi/llm/ollama.py
+++ b/navi/llm/ollama.py
@@ -71,7 +71,10 @@
             return LLMModelNotFoundError(str(e))
         return LLMBackendError(str(e))
     # Catch httpx / socket connection failures by message
+    err_type = type(e).__name__.lower()
     err_str = str(e).lower()
+    if "timeout" in err_type:
+        return LLMConnectionError(str(e) or type(e).__name__)
     if any(kw in err_str for kw in ("connect", "connection refused", "name or service not known",
                                      "network", "timeout", "unreachable", "nodename")):
         return LLMConnectionError(str(e))
diff --git a/tests/unit/core/test_registry.py b/tests/unit/core/test_registry.py
index 9737488..bed9e98 100644
--- a/tests/unit/core/test_registry.py
+++ b/tests/unit/core/test_registry.py
@@ -3,6 +3,7 @@
 import pytest
 
 from navi.core.registry import BackendRegistry, ProfileRegistry, ToolRegistry
+from navi.context_providers import ContextProviderRegistry
 from navi.exceptions import ProfileNotFound, ToolNotFound
 from tests.conftest_factory import FakeLLMBackend, FakeTool, make_profile
 
@@ -77,3 +78,45 @@
         reg.register("a", FakeLLMBackend())
         reg.register("b", FakeLLMBackend())
         assert sorted(reg.all_keys()) == ["a", "b"]
+
+
+class TestBackendDiscovery:
+    def test_primary_ollama_uses_expanded_timeout(self, monkeypatch):
+        import navi.core.registry as registry_mod
+
+        captured = {}
+
+        class FakeOllamaBackend:
+            def __init__(self, **kwargs):
+                captured.update(kwargs)
+
+        monkeypatch.setattr(registry_mod.settings, "ollama_backends_file", "")
+        monkeypatch.setattr(registry_mod.settings, "openai_api_key", "")
+        monkeypatch.setattr(registry_mod.settings, "ollama_request_timeout", 30)
+        monkeypatch.setattr(registry_mod.settings, "llm_complete_timeout", 120)
+        monkeypatch.setattr(registry_mod.settings, "llm_stream_first_chunk_timeout", 180)
+
+        import navi.llm.ollama as ollama_mod
+
+        monkeypatch.setattr(ollama_mod, "OllamaBackend", FakeOllamaBackend)
+
+        discovered = registry_mod._discover_backends()
+
+        assert discovered[0][0] == "ollama"
+        assert captured["timeout"] == 180
+
+
+class TestContextProviderRegistry:
+    def test_all_returns_registered_providers(self):
+        reg = ContextProviderRegistry()
+
+        class Provider:
+            name = "provider"
+            description = "Provider"
+
+            async def get_context(self):
+                return None
+
+        reg.register(Provider)
+
+        assert reg.all() == [Provider]
diff --git a/tests/unit/llm/test_ollama.py b/tests/unit/llm/test_ollama.py
new file mode 100644
index 0000000..e3ed91b
--- /dev/null
+++ b/tests/unit/llm/test_ollama.py
@@ -0,0 +1,43 @@
+"""Unit tests for Ollama backend helpers."""
+
+import httpx
+
+from navi.exceptions import LLMConnectionError
+from navi.llm.fallback import FallbackOllamaBackend, ServerEntry
+from navi.llm.ollama import _classify_error
+
+
+def test_classify_read_timeout_as_connection_error():
+    err = _classify_error(httpx.ReadTimeout("timed out"))
+
+    assert isinstance(err, LLMConnectionError)
+
+
+def test_classify_empty_timeout_message_as_connection_error():
+    err = _classify_error(httpx.ReadTimeout(""))
+
+    assert isinstance(err, LLMConnectionError)
+    assert str(err) == "ReadTimeout"
+
+
+def test_fallback_client_uses_expanded_timeout(monkeypatch):
+    import navi.llm.fallback as fallback_mod
+    import navi.config as config_mod
+
+    captured = {}
+
+    class FakeOllamaBackend:
+        def __init__(self, **kwargs):
+            captured.update(kwargs)
+
+    monkeypatch.setattr(fallback_mod, "OllamaBackend", FakeOllamaBackend)
+    monkeypatch.setattr(config_mod.settings, "ollama_request_timeout", 30)
+    monkeypatch.setattr(config_mod.settings, "llm_complete_timeout", 120)
+    monkeypatch.setattr(config_mod.settings, "llm_stream_first_chunk_timeout", 180)
+
+    backend = FallbackOllamaBackend([ServerEntry(host="http://ollama.test")])
+    backend._get_client(ServerEntry(host="http://ollama.test", api_key="secret"))
+
+    assert captured["host"] == "http://ollama.test"
+    assert captured["api_key"] == "secret"
+    assert captured["timeout"] == 180
diff --git a/tests/unit/test_content_store.py b/tests/unit/test_content_store.py
new file mode 100644
index 0000000..121800a
--- /dev/null
+++ b/tests/unit/test_content_store.py
@@ -0,0 +1,65 @@
+"""Unit tests for session content metadata store."""
+
+import pytest
+
+import navi.content_store as content_store
+from tests.conftest_factory import FakeConnection, FakePool
+
+
+class TestEnsureTables:
+    async def test_creates_session_content_table_and_indexes(self, monkeypatch):
+        conn = FakeConnection()
+
+        async def fake_pool():
+            return FakePool(conn)
+
+        monkeypatch.setattr(content_store, "_get_db_pool", fake_pool)
+
+        await content_store.ensure_tables()
+
+        executed = "\n".join(call[1] for call in conn.calls if call[0] == "execute")
+        assert "CREATE TABLE IF NOT EXISTS session_content" in executed
+        assert "idx_session_content_session" in executed
+        assert "CREATE UNIQUE INDEX IF NOT EXISTS idx_session_content_file" in executed
+        assert "ON session_content (session_id, filename)" in executed
+
+
+class TestPublish:
+    @pytest.fixture(autouse=True)
+    def _session_dir(self, monkeypatch, tmp_path):
+        monkeypatch.setattr(content_store.settings, "session_files_dir", str(tmp_path / "sessions"))
+        monkeypatch.setattr(content_store.settings, "public_url", "http://localhost:8000")
+
+    async def test_upserts_by_session_and_filename(self, monkeypatch, tmp_path):
+        conn = FakeConnection()
+        conn.enqueue("INSERT 0 1")
+
+        async def fake_pool():
+            return FakePool(conn)
+
+        monkeypatch.setattr(content_store, "_get_db_pool", fake_pool)
+        sess_dir = tmp_path / "sessions" / "sess-1"
+        sess_dir.mkdir(parents=True)
+        (sess_dir / "logo.svg").write_text("<svg></svg>")
+
+        info = await content_store.publish(
+            session_id="sess-1",
+            filename="logo.svg",
+            title="Logo",
+        )
+
+        assert info["id"] == "sess-1_logo.svg"
+        assert info["url"] == "http://localhost:8000/sessions/sess-1/files/logo.svg"
+        call = conn.calls[0]
+        assert call[0] == "execute"
+        assert "ON CONFLICT (session_id, filename) DO UPDATE" in call[1]
+        assert call[2][1:5] == ("sess-1", "logo.svg", "svg", "Logo")
+
+    async def test_missing_file_raises(self, monkeypatch, tmp_path):
+        async def fake_pool():
+            return FakePool(FakeConnection())
+
+        monkeypatch.setattr(content_store, "_get_db_pool", fake_pool)
+
+        with pytest.raises(FileNotFoundError):
+            await content_store.publish(session_id="sess-1", filename="missing.svg")
diff --git a/tests/unit/tools/test_content_publish.py b/tests/unit/tools/test_content_publish.py
new file mode 100644
index 0000000..6471647
--- /dev/null
+++ b/tests/unit/tools/test_content_publish.py
@@ -0,0 +1,78 @@
+"""Unit tests for content_publish tool."""
+
+import pytest
+
+import navi.tools.content_publish as content_publish_mod
+from navi.tools.base import current_session_id
+from navi.tools.content_publish import ContentPublishTool
+
+
+class TestContentPublishTool:
+    @pytest.fixture
+    def tool(self, monkeypatch, tmp_path):
+        monkeypatch.setattr(content_publish_mod.settings, "session_files_dir", str(tmp_path / "sessions"))
+        token = current_session_id.set("sess-1")
+        try:
+            yield ContentPublishTool()
+        finally:
+            current_session_id.reset(token)
+
+    async def test_requires_active_session(self):
+        token = current_session_id.set(None)
+        try:
+            result = await ContentPublishTool().execute({"filename": "logo.svg"})
+        finally:
+            current_session_id.reset(token)
+
+        assert not result.success
+        assert result.error == "no_session"
+
+    async def test_missing_file_reports_session_dir(self, tool, tmp_path):
+        result = await tool.execute({"filename": "missing.svg"})
+
+        assert not result.success
+        assert result.error == "not_found"
+        assert str(tmp_path / "sessions" / "sess-1") in result.output
+        assert "SESSION_FILES_DIR" in result.output
+
+    async def test_rejects_directory(self, tool, tmp_path):
+        sess_dir = tmp_path / "sessions" / "sess-1"
+        (sess_dir / "folder").mkdir(parents=True)
+
+        result = await tool.execute({"filename": "folder"})
+
+        assert not result.success
+        assert result.error == "not_a_file"
+
+    async def test_strips_path_components_and_publishes(self, tool, monkeypatch, tmp_path):
+        sess_dir = tmp_path / "sessions" / "sess-1"
+        sess_dir.mkdir(parents=True)
+        (sess_dir / "logo.svg").write_text("<svg></svg>")
+        calls = []
+
+        async def fake_publish(**kwargs):
+            calls.append(kwargs)
+            return {
+                "id": "content-id",
+                "url": "http://localhost:8000/sessions/sess-1/files/logo.svg",
+                "filename": kwargs["filename"],
+                "content_type": kwargs["content_type"] or "svg",
+                "title": kwargs["title"] or kwargs["filename"],
+            }
+
+        monkeypatch.setattr(content_publish_mod, "publish", fake_publish)
+
+        result = await tool.execute({
+            "filename": "../logo.svg",
+            "title": "Logo",
+            "content_type": "svg",
+        })
+
+        assert result.success
+        assert calls == [{
+            "session_id": "sess-1",
+            "filename": "logo.svg",
+            "title": "Logo",
+            "content_type": "svg",
+        }]
+        assert result.metadata["filename"] == "logo.svg"