diff --git a/pkg/service/health/checks_cert_chain.go b/pkg/service/health/checks_cert_chain.go
index d27ddc4..6568a69 100644
--- a/pkg/service/health/checks_cert_chain.go
+++ b/pkg/service/health/checks_cert_chain.go
@@ -29,6 +29,10 @@ const CheckIDCertChain = "service_cert_chain"
 //     something else → warning with an `openssl s_client`
 //     investigation prompt (foreign chain / reverse proxy /
 //     ingress cert).
+//   - endpoint not reachable from inside the service (no cert
+//     presented) → warning, not error: the advertised HTTPS URL
+//     is often intentionally unreachable from the service itself
+//     (reverse proxy, Docker-published port, LAN-only hostname).
 //   - HTTPS URL not configured → skip silently.
 //
 // caCertFn returns AfterTouch's own CA leaf certificate (nil if
@@ -82,10 +86,27 @@ func runCertChainCheck(httpsURL string, caCertFn func() *x509.Certificate) []Fin
 	// reachability problem.
 	leaf := leafFromVerifyError(err)
 	if leaf == nil {
+		// The dial failed before any certificate was presented
+		// (connection refused, timeout, handshake reset). From
+		// inside the service we can't tell "the endpoint is down"
+		// apart from "the advertised HTTPS URL simply isn't
+		// reachable from here" — the latter is a normal, healthy
+		// setup (TLS terminated by a reverse proxy, or a
+		// Docker-published port / external hostname that only
+		// resolves on the LAN). Reporting a hard error there is a
+		// false alarm (issue #355), so this is a warning with the
+		// context to tell the two apart.
 		return []Finding{{
-			Severity: SeverityError,
-			Message:  fmt.Sprintf("Could not connect to %s: %v", addr, err),
-			Details:  "AfterTouch's HTTPS endpoint isn't reachable from inside the service, or the peer dropped the handshake before presenting a certificate. Check that the listener is bound and the URL host:port resolves correctly.",
+			Severity: SeverityWarning,
+			Message:  fmt.Sprintf("Configured HTTPS endpoint %s isn't reachable from inside the service.", addr),
+			Details: fmt.Sprintf("AfterTouch dialed its own configured HTTPS URL (%s) and the connection failed before any certificate was presented: %v. "+
+				"This is expected — and not a problem — if TLS is terminated by a reverse proxy in front of AfterTouch, or the advertised HTTPS URL isn't reachable from inside the container (for example a Docker-published port, or a hostname that only resolves elsewhere on your network). In that case, verify the endpoint from a client instead (see below). "+
+				"If AfterTouch is meant to serve HTTPS directly, check that the HTTPS listener is bound and that the URL host:port is correct.", httpsURL, err),
+			ManualCommands: []ManualCommand{{
+				Label:   "Verify the endpoint from a machine on your network:",
+				Command: fmt.Sprintf("openssl s_client -connect %s -servername %s </dev/null", addr, host),
+				Hint:    "Run from a client that reaches the advertised URL (not necessarily the service host). A successful handshake there means the endpoint is fine and this warning is expected for your setup.",
+			}},
 		}}
 	}
 
diff --git a/pkg/service/health/checks_cert_chain_test.go b/pkg/service/health/checks_cert_chain_test.go
index aab0514..3d70daa 100644
--- a/pkg/service/health/checks_cert_chain_test.go
+++ b/pkg/service/health/checks_cert_chain_test.go
@@ -29,11 +29,27 @@ func TestCertChain_UnparseableURLWarns(t *testing.T) {
 	}
 }
 
-func TestCertChain_UnreachableEndpoint(t *testing.T) {
-	// 127.0.0.1:1 refuses; using https:// to force TLS path.
+func TestCertChain_UnreachableEndpoint_IsWarningNotError(t *testing.T) {
+	// Regression for issue #355: the service dialing its own
+	// configured HTTPS URL and finding it unreachable is NOT a hard
+	// error. The advertised URL is frequently unreachable from
+	// inside the service on purpose (TLS terminated by a reverse
+	// proxy, a Docker-published port, or a LAN-only hostname), so a
+	// red error there is a false alarm. It must be a warning that
+	// explains the expected case and offers a client-side check.
+	//
+	// 127.0.0.1:1 refuses; using https:// to force the TLS path.
 	got := runCertChainCheck("https://127.0.0.1:1/", nil)
-	if len(got) != 1 || got[0].Severity != SeverityError {
-		t.Fatalf("expected one error for unreachable endpoint, got %+v", got)
+	if len(got) != 1 || got[0].Severity != SeverityWarning {
+		t.Fatalf("expected one warning for unreachable endpoint, got %+v", got)
+	}
+
+	if !strings.Contains(got[0].Details, "reverse proxy") {
+		t.Errorf("expected details to name the reverse-proxy / unreachable-advertised-URL case, got %q", got[0].Details)
+	}
+
+	if len(got[0].ManualCommands) == 0 || !strings.Contains(got[0].ManualCommands[0].Command, "openssl s_client") {
+		t.Errorf("expected an openssl s_client client-side verification command, got %+v", got[0].ManualCommands)
 	}
 }