diff --git a/docs/release-control/v6/internal/subsystems/notifications.md b/docs/release-control/v6/internal/subsystems/notifications.md
index 57e75b308..ba728e1d0 100644
--- a/docs/release-control/v6/internal/subsystems/notifications.md
+++ b/docs/release-control/v6/internal/subsystems/notifications.md
@@ -700,6 +700,10 @@ actual rate-limit log output. These queue-free tests establish local diagnostic
 redaction, not destination receipt, installed recovery or release qualification.
 No claim is made that arbitrary custom path/query secrets are recognised.
 
+Delivery-log errors use `RedactWebhookDiagnosticSecrets` so URLs embedded in
+otherwise useful error text receive the same masking without discarding the
+surrounding status context. Malformed embedded URLs still fail closed.
+
 ### Slack webhook diagnostic path confidentiality
 
 The same helper masks paths on the exact `hooks.slack.com` and
diff --git a/internal/api/alerting/notifications.go b/internal/api/alerting/notifications.go
index 31ab95e15..dcf32bd1e 100644
--- a/internal/api/alerting/notifications.go
+++ b/internal/api/alerting/notifications.go
@@ -1076,7 +1076,7 @@ func (h *NotificationHandlers) GetDeliveryLog(w http.ResponseWriter, r *http.Req
 	// can embed credentials.
 	for i := range entries {
 		if entries[i].ErrorMessage != "" {
-			entries[i].ErrorMessage = notifications.RedactWebhookURLSecrets(entries[i].ErrorMessage)
+			entries[i].ErrorMessage = notifications.RedactWebhookDiagnosticSecrets(entries[i].ErrorMessage)
 		}
 	}
 
diff --git a/internal/notifications/webhook_url_redaction.go b/internal/notifications/webhook_url_redaction.go
index 26ba2f75e..019ec41f5 100644
--- a/internal/notifications/webhook_url_redaction.go
+++ b/internal/notifications/webhook_url_redaction.go
@@ -6,6 +6,8 @@ import (
 	"strings"
 )
 
+const invalidWebhookURLDiagnostic = "[invalid webhook URL]"
+
 // RedactWebhookURLSecrets masks credentials commonly embedded in webhook URLs
 // while preserving the URL shape needed for operator diagnostics.
 func RedactWebhookURLSecrets(urlString string) string {
@@ -14,7 +16,7 @@ func RedactWebhookURLSecrets(urlString string) string {
 	// URLs rather than returning unparsed credentials to diagnostic callers.
 	parsed, err := url.Parse(urlString)
 	if err != nil {
-		return "[invalid webhook URL]"
+		return invalidWebhookURLDiagnostic
 	}
 	if parsed.User != nil {
 		parsed.User = url.User("REDACTED")
@@ -91,6 +93,49 @@ func RedactWebhookURLSecrets(urlString string) string {
 	return urlString
 }
 
+// RedactWebhookDiagnosticSecrets masks webhook URLs embedded in diagnostic
+// text while retaining the non-secret context around them. A malformed URL
+// still fails closed rather than returning potentially sensitive text.
+func RedactWebhookDiagnosticSecrets(message string) string {
+	lowerMessage := strings.ToLower(message)
+	cursor := 0
+	foundURL := false
+	var redacted strings.Builder
+
+	for cursor < len(message) {
+		httpOffset := strings.Index(lowerMessage[cursor:], "http://")
+		httpsOffset := strings.Index(lowerMessage[cursor:], "https://")
+		offset := httpOffset
+		if offset == -1 || (httpsOffset != -1 && httpsOffset < offset) {
+			offset = httpsOffset
+		}
+		if offset == -1 {
+			break
+		}
+
+		start := cursor + offset
+		end := len(message)
+		if whitespace := strings.IndexAny(message[start:], " \t\r\n"); whitespace != -1 {
+			end = start + whitespace
+		}
+
+		redactedURL := RedactWebhookURLSecrets(message[start:end])
+		if redactedURL == invalidWebhookURLDiagnostic {
+			return invalidWebhookURLDiagnostic
+		}
+		redacted.WriteString(message[cursor:start])
+		redacted.WriteString(redactedURL)
+		cursor = end
+		foundURL = true
+	}
+
+	if !foundURL {
+		return RedactWebhookURLSecrets(message)
+	}
+	redacted.WriteString(message[cursor:])
+	return redacted.String()
+}
+
 func redactWebhookTransportError(err error) error {
 	if err == nil {
 		return nil
diff --git a/internal/notifications/webhook_url_redaction_test.go b/internal/notifications/webhook_url_redaction_test.go
index ec2ff8290..7f871ac30 100644
--- a/internal/notifications/webhook_url_redaction_test.go
+++ b/internal/notifications/webhook_url_redaction_test.go
@@ -72,6 +72,38 @@ func TestRedactWebhookURLSecrets(t *testing.T) {
 	}
 }
 
+func TestRedactWebhookDiagnosticSecrets(t *testing.T) {
+	tests := map[string]struct {
+		input string
+		want  string
+	}{
+		"embedded query credential": {
+			input: "post https://hooks.example.test/notify?token=supersecret returned 401",
+			want:  "post https://hooks.example.test/notify?token=REDACTED returned 401",
+		},
+		"embedded userinfo": {
+			input: "request to https://hook-user:hook-password@example.test/hook failed",
+			want:  "request to https://REDACTED@example.test/hook failed",
+		},
+		"plain diagnostic": {
+			input: "connection refused",
+			want:  "connection refused",
+		},
+		"malformed embedded URL": {
+			input: "post https://hook-user:hook-password@example.test/%zz failed",
+			want:  invalidWebhookURLDiagnostic,
+		},
+	}
+
+	for name, test := range tests {
+		t.Run(name, func(t *testing.T) {
+			if got := RedactWebhookDiagnosticSecrets(test.input); got != test.want {
+				t.Fatalf("RedactWebhookDiagnosticSecrets() = %q, want %q", got, test.want)
+			}
+		})
+	}
+}
+
 func TestRedactWebhookTransportErrorPreservesBehaviorWithoutToken(t *testing.T) {
 	cause := errors.New("connection refused")
 	original := &url.Error{