diff --git a/ROADMAP.md b/ROADMAP.md
index ed40fdc3e..921a0ffd4 100644
--- a/ROADMAP.md
+++ b/ROADMAP.md
@@ -889,7 +889,7 @@ graph LR
 | Token-efficiency benchmark: measured savings, published results | In progress | P1 | 62/64 (97%) | [103-token-bench](./specs/103-token-bench/) |  |
 | Telemetry identity & data quality (machine_id + CI-filter hardening) | In progress | P1 | — |  |  |
 | Telemetry v7: honest funnel + churn instrumentation | In progress | P1 | — | [080-telemetry-v7-churn](./specs/080-telemetry-v7-churn/) |  |
-| MCP protocol upgrade to 2026-07-28 revision | In progress | P1 | 19/81 (23%) | [058-mcp-2026-upgrade](./specs/058-mcp-2026-upgrade/) |  |
+| MCP protocol upgrade to 2026-07-28 revision | In progress | P1 | 21/81 (26%) | [058-mcp-2026-upgrade](./specs/058-mcp-2026-upgrade/) |  |
 | Planning/docs truth automation | In progress | P2 | — |  |  |
 | Discovery-quality eval harness (Spec 065 second half) | In progress | P3 | — | [065-evaluation-foundation](./specs/065-evaluation-foundation/) |  |
 | tpa-db: versioned TPA signature database for the offline scanner | Todo | P1 | — | [101-tpa-db](./specs/101-tpa-db/) |  |
@@ -992,7 +992,7 @@ Legend: `shipped` ≥95% checked · `in-flight` 1–94% · `drafted` 0% · `—`
 | [055-frontend-major-upgrades](./specs/055-frontend-major-upgrades/) | `shipped` | 23/24 (96%) |
 | [056-output-schema-validation](./specs/056-output-schema-validation/) | `in-flight` | 22/24 (92%) |
 | [057-in-proxy-profiles](./specs/057-in-proxy-profiles/) | `in-flight` | 20/25 (80%) |
-| [058-mcp-2026-upgrade](./specs/058-mcp-2026-upgrade/) | `in-flight` | 19/81 (23%) |
+| [058-mcp-2026-upgrade](./specs/058-mcp-2026-upgrade/) | `in-flight` | 21/81 (26%) |
 | [059-output-sanitisation](./specs/059-output-sanitisation/) | `shipped` | 24/25 (96%) |
 | [060-settings-page](./specs/060-settings-page/) | `shipped` | 16/16 (100%) |
 | [064-glass-cockpit](./specs/064-glass-cockpit/) | — | — |
diff --git a/internal/server/cache_hints_test.go b/internal/server/cache_hints_test.go
new file mode 100644
index 000000000..cf89badca
--- /dev/null
+++ b/internal/server/cache_hints_test.go
@@ -0,0 +1,119 @@
+package server
+
+import (
+	"bytes"
+	"context"
+	"encoding/json"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+
+	"github.com/mark3labs/mcp-go/mcp"
+	mcpserver "github.com/mark3labs/mcp-go/server"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/smart-mcp-proxy/mcpproxy-go/internal/config"
+)
+
+// Spec 058 FR-019 / Spec 113-f: list and read results must carry ttlMs and a
+// cacheScope. Every mcpproxy listing is caller-dependent (profile, agent-token
+// scope, quarantine state), so the scope must be private and the TTL short.
+//
+// The production client-facing transport is pinned to the legacy era
+// (FR-028), where the hints are not emitted, so this test drives a server built
+// with the production hint options over an unpinned transport.
+
+func cacheHintTestServer(t *testing.T) *httptest.Server {
+	t.Helper()
+	opts := append([]mcpserver.ServerOption{
+		mcpserver.WithToolCapabilities(true),
+		mcpserver.WithResourceCapabilities(true, true),
+		mcpserver.WithPromptCapabilities(true),
+	}, cacheHintServerOptions()...)
+	srv := mcpserver.NewMCPServer("cache-hint-probe", "1.0.0", opts...)
+	srv.AddTool(mcp.NewTool("probe"), func(context.Context, mcp.CallToolRequest) (*mcp.CallToolResult, error) {
+		return mcp.NewToolResultText("ok"), nil
+	})
+	hs := httptest.NewServer(mcpserver.NewStreamableHTTPServer(srv))
+	t.Cleanup(hs.Close)
+	return hs
+}
+
+func postModernCacheProbe(t *testing.T, url string, method mcp.MCPMethod, params map[string]any) map[string]any {
+	t.Helper()
+	params["_meta"] = map[string]any{
+		mcp.MetaKeyProtocolVersion:    mcp.ProtocolVersion20260728,
+		mcp.MetaKeyClientInfo:         map[string]any{"name": "t", "version": "1"},
+		mcp.MetaKeyClientCapabilities: map[string]any{},
+	}
+	body, err := json.Marshal(map[string]any{"jsonrpc": "2.0", "id": 1, "method": method, "params": params})
+	require.NoError(t, err)
+	req, err := http.NewRequestWithContext(t.Context(), http.MethodPost, url, bytes.NewReader(body))
+	require.NoError(t, err)
+	req.Header.Set("Content-Type", "application/json")
+	req.Header.Set("Accept", "application/json, text/event-stream")
+	req.Header.Set(mcp.HeaderProtocolVersion, mcp.ProtocolVersion20260728)
+	req.Header.Set(mcp.HeaderMethod, string(method))
+	raw, _ := json.Marshal(params)
+	if name, ok := mcp.ExtractHeaderName(method, raw); ok {
+		enc, ok := mcp.EncodeHeaderValue(name)
+		require.True(t, ok)
+		req.Header.Set(mcp.HeaderName, enc)
+	}
+	resp, err := http.DefaultClient.Do(req)
+	require.NoError(t, err)
+	defer resp.Body.Close()
+	var msg map[string]any
+	require.NoError(t, json.NewDecoder(resp.Body).Decode(&msg))
+	result, ok := msg["result"].(map[string]any)
+	require.True(t, ok, "expected result for %s, got %v", method, msg)
+	return result
+}
+
+func TestListResultsCarryPrivateShortCacheHints(t *testing.T) {
+	hs := cacheHintTestServer(t)
+
+	for _, method := range []mcp.MCPMethod{
+		mcp.MethodToolsList,
+		mcp.MethodPromptsList,
+		mcp.MethodResourcesList,
+		mcp.MethodResourcesTemplatesList,
+	} {
+		t.Run(string(method), func(t *testing.T) {
+			result := postModernCacheProbe(t, hs.URL, method, map[string]any{})
+			assert.Equal(t, string(mcp.CacheScopePrivate), result["cacheScope"],
+				"mcpproxy listings depend on profile/token scope, so they must never be public")
+			assert.Equal(t, float64(mcpListCacheTTLMs), result["ttlMs"])
+		})
+	}
+}
+
+func TestCacheHintTTLIsShort(t *testing.T) {
+	assert.Positive(t, mcpListCacheTTLMs)
+	assert.LessOrEqual(t, mcpListCacheTTLMs, int64(10_000),
+		"listings change with quarantine/profile state; keep the freshness window conservative")
+}
+
+// TestRoutingModeServersCarryCacheHints pins that the real servers behind
+// /mcp, /mcp/all, /mcp/code and /mcp/call (not just p.server) advertise the
+// private hints. Served over an unpinned transport because the production
+// transport is pinned to the legacy era (FR-028).
+func TestRoutingModeServersCarryCacheHints(t *testing.T) {
+	proxy, _ := newStoredScriptProxyCfg(t, nil)
+	for _, mode := range []string{
+		config.RoutingModeRetrieveTools,
+		config.RoutingModeCodeExecution,
+		config.RoutingModeDirect,
+	} {
+		t.Run(mode, func(t *testing.T) {
+			srv := proxy.GetMCPServerForMode(mode)
+			require.NotNil(t, srv)
+			hs := httptest.NewServer(mcpserver.NewStreamableHTTPServer(srv))
+			t.Cleanup(hs.Close)
+			result := postModernCacheProbe(t, hs.URL, mcp.MethodToolsList, map[string]any{})
+			assert.Equal(t, string(mcp.CacheScopePrivate), result["cacheScope"])
+			assert.Equal(t, float64(mcpListCacheTTLMs), result["ttlMs"])
+		})
+	}
+}
diff --git a/internal/server/mcp.go b/internal/server/mcp.go
index b43048f14..17fe848df 100644
--- a/internal/server/mcp.go
+++ b/internal/server/mcp.go
@@ -613,6 +613,9 @@ func NewMCPProxyServer(
 		capabilities = append(capabilities, mcpserver.WithPromptCapabilities(true))
 	}
 
+	// Spec 058 FR-019: explicit, private, short-lived cache hints.
+	capabilities = append(capabilities, cacheHintServerOptions()...)
+
 	// Add server instructions for AI agent guidance
 	capabilities = append(capabilities, mcpserver.WithInstructions(resolveInstructions(config.Instructions)))
 
@@ -8348,3 +8351,33 @@ func forwardHeadersWriteError(names []string, static map[string]string) error {
 	}
 	return fmt.Errorf("invalid forward_headers: %s", strings.Join(msgs, "; "))
 }
+
+// mcpListCacheTTLMs is the freshness window (SEP-2549 ttlMs) advertised on
+// mcpproxy's list and read results. Listings change with quarantine approvals,
+// profile switches and upstream reconnects (list_changed covers connected
+// sessions), so the window is deliberately short.
+const mcpListCacheTTLMs int64 = 5000
+
+// cacheHintServerOptions returns the SEP-2549 cache-hint options for the proxy
+// MCP server (Spec 058 FR-019). Every cacheable surface is private: tools/list,
+// prompts/list and resources/* are filtered per caller by profile (Spec 108),
+// agent-token scope (Spec 105) and per-tool quarantine, so no result is
+// provably caller-independent and none may be shared across authorization
+// contexts. Per-method hints are set explicitly so a change to the library
+// default cannot silently widen the scope.
+func cacheHintServerOptions() []mcpserver.ServerOption {
+	opts := []mcpserver.ServerOption{
+		mcpserver.WithCacheHints(mcpListCacheTTLMs, mcp.CacheScopePrivate),
+	}
+	for _, m := range []mcp.MCPMethod{
+		mcp.MethodToolsList,
+		mcp.MethodPromptsList,
+		mcp.MethodResourcesList,
+		mcp.MethodResourcesTemplatesList,
+		mcp.MethodResourcesRead,
+		mcp.MethodServerDiscover,
+	} {
+		opts = append(opts, mcpserver.WithMethodCacheHints(m, mcpListCacheTTLMs, mcp.CacheScopePrivate))
+	}
+	return opts
+}
diff --git a/internal/server/mcp_routing.go b/internal/server/mcp_routing.go
index b88b5e374..4a1b2dac5 100644
--- a/internal/server/mcp_routing.go
+++ b/internal/server/mcp_routing.go
@@ -1191,6 +1191,9 @@ func (p *MCPProxyServer) initRoutingModeServers() {
 		mcpserver.WithToolCapabilities(true),
 		mcpserver.WithRecovery(),
 	}
+	// Spec 058 FR-019: private short-lived cache hints on every routing-mode
+	// server (shared opts, so directOpts inherits them too).
+	opts = append(opts, cacheHintServerOptions()...)
 	if p.hooks != nil {
 		// Spec 105 FR-010 D13/gap G6: mark which real JSON-RPC method
 		// produced this request — mcp-go calls these with the SAME ctx it
diff --git a/specs/058-mcp-2026-upgrade/tasks.md b/specs/058-mcp-2026-upgrade/tasks.md
index b3ce07614..ec3b933f2 100644
--- a/specs/058-mcp-2026-upgrade/tasks.md
+++ b/specs/058-mcp-2026-upgrade/tasks.md
@@ -153,8 +153,8 @@ Single Go project. Backend paths are repo-relative: `internal/`, `cmd/`, `bench/
 
 **Independent test**: inspect list/read responses for valid hints; compare repeated `tools/list` results for stable ordering; confirm trace ids reach activity records.
 
-- [ ] T063 [P] [US5] Write failing tests that list/read responses carry `ttlMs` and an identity-appropriate `cacheScope`, in `internal/server/cache_hints_test.go`
-- [ ] T064 [US5] Configure cache hints — private for identity-scoped surfaces, public for shared ones — in `internal/server/mcp_routing.go` and `internal/server/mcp.go`
+- [x] T063 [P] [US5] Write failing tests that list/read responses carry `ttlMs` and an identity-appropriate `cacheScope`, in `internal/server/cache_hints_test.go`
+- [x] T064 [US5] Configure cache hints — private for identity-scoped surfaces, public for shared ones — in `internal/server/mcp_routing.go` and `internal/server/mcp.go`
 - [ ] T065 [P] [US5] Write a failing test that repeated `tools/list` calls are byte-identical under unchanged state, in `internal/server/stateless_list_test.go`
 - [ ] T066 [US5] Make tool ordering deterministic wherever map iteration currently leaks in, in `internal/server/mcp_routing.go`
 - [ ] T067 [P] [US5] Write a failing test that external `$ref`s are not dereferenced and that schemas validate as JSON Schema 2020-12, in `internal/server/mcp_input_validation_test.go`