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Monitoring is not just a tool for managed hosting—it’s part of the product. Customers are not just buying infrastructure; they are buying the assurance that availability, security, and responsiveness are always maintained. This is where many monitoring setups fail as they grow: what is initially “sufficient” becomes an operational bottleneck and, at worst, the cause of escalations.
In this post, we illustrate through an anonymized project how ayedo modernized the endpoint monitoring of a managed hosting provider. The client remains anonymous, but the approach is transferable—especially for organizations that operate many endpoints, need to demonstrate SLAs, and want to remain GDPR compliant.
The client operates web applications, management portals, e-commerce platforms, and API backends for medium-sized organizations, including systems with high availability and security requirements, such as in the public sector and healthcare. In operation, this means: many endpoints, many dependencies, many integrations—and very little error tolerance on the client side.
The monitoring had grown historically. On one hand, there was a self-hosted Nagios setup, and on the other, an inexpensive US-based uptime service that performed external checks. This combination worked in the early years, but as the customer portfolio grew, the weaknesses became increasingly apparent.
The first structural flaw was the monitoring location. The Nagios checks ran from a single server in the same data center where most of the customer environments were operated. This meant the monitoring was effectively “inside.” As soon as there were brief routing changes, firewall updates, or internal network disruptions, Nagios reported outages, even though the endpoint was still accessible to real end users. Conversely, the monitoring was blind to regional issues outside the data center—exactly the type of errors that modern web systems are particularly prone to: DNS issues, CDN misconfigurations, peering problems, or regional provider disruptions.
The result was 30 to 50 alerts daily, more than a quarter of which were false alarms. And this is where the real problem began: alert fatigue. When a team experiences too many false alarms, they lose trust in the signal. Alerts are ignored, acknowledged later, or postponed to “we’ll deal with it eventually.” This is not human failure but systemic. Monitoring that is not precise does not create security but noise.
The second flaw was content-related: the monitoring essentially checked “HTTP 200 or not.” This can roughly capture availability but misses exactly the issues that customers today expect as professionalism. If a certificate expires in three days, the endpoint is technically accessible—but effectively broken. If TLS parameters are insecure or security headers are missing, the site runs—until the auditor comes or a penetration test escalates.
The third problem was operational: certificate management was “mostly automated” via Let’s Encrypt and Certbot, but automation without monitoring is a gamble. Failures due to DNS challenges, rate limits, or configuration drift remain invisible until the certificate actually expires. And then it typically happens exactly when it hurts the most: Friday evening, weekend operations, escalating hotline, angry customer.
The fourth problem was the lack of performance visibility. An endpoint can be “OK” and yet practically unusable because response times increase, timeouts accumulate, or individual regions become massively slower. Without response time metrics and trend data, this degradation goes unnoticed until it becomes an incident.
And above all, there was one issue that is non-negotiable in regulated industries: GDPR. The US uptime service transferred monitoring data to the USA. This sounds harmless until you realize what can be contained in monitoring data: URLs, headers, status codes—sometimes even session IDs or specific paths that allow conclusions. Several customers objected to this exact point and demanded the complete abandonment of US-based tools.
The incident that accelerated everything was classic and simultaneously particularly delicate: a public administration portal was inaccessible to users in southern Germany for four hours due to a DNS misconfiguration. Meanwhile, the internal monitoring from the Frankfurt data center continuously reported “OK.” The escalation was correspondingly clear: monitoring that does not detect regional outages is not suitable for critical portals.
The customer’s demand was clear: multi-region monitoring with verifiably low false-positive rates, TLS monitoring, security checks, and GDPR-compliant infrastructure.
This is where we, as ayedo, stepped in.
We did not understand the problem as “replacing Nagios.” We understood it as restoring a reliable signal. An alert must again mean: something is really wrong. And monitoring must do more than “run”: it must make security risks and degrading performance visible before they become incidents.
Therefore, we provided endpoint monitoring as a managed service—with three central features:
First: checks from multiple, independent points of presence to reliably detect regional errors and drastically reduce false alarms. Second: security awareness as standard: TLS, certificate expiration, cipher suites, and security headers are continuously checked. Third: integration capability: the data must be exportable to existing observability stacks so that reporting and dashboards do not have to be built manually.
The core mechanism is multi-region monitoring with global PoPs. Each endpoint is not checked from a single location but in parallel from multiple independent locations in Europe, America, and Asia. This creates a realistic picture of how end users actually experience the service.
The crucial difference lies in the alert logic. An outage is not reported on a single failed check but only when multiple PoPs independently confirm that the endpoint is not reachable. Additionally, intelligent retry mechanisms are in place to prevent short-term jitter effects—such as transient packet loss or brief DNS fluctuations—from immediately becoming an incident.
The result is not just “fewer alarms.” It is a qualitatively different signal. The operations team can take alerts seriously again because an alert no longer means “maybe” but “verified.” At the same time, regional outages become visible because the checks can report differentiated: reachable from Region A, not reachable from Region B. This differentiation was not possible in the previous DNS incident.
A second major lever was the TLS/SSL security check. For each HTTPS endpoint, we continuously check the certificate validity with configurable advance alerting, typically 14 days before expiration. This shifts operations from “firefighting” to “planning.” If a Let’s Encrypt renewal fails, it’s no longer a Friday night drama but a ticket with sufficient lead time.
Furthermore, we check TLS versions and warn of outdated configurations, as well as insecure cipher suites or incomplete certificate chains. In regulated environments, this is more than hygiene: it is audit capability. The difference between “we believe TLS is okay” and “we can permanently demonstrate the state” is enormous.
Many security issues are not “patch now immediately,” but “could have been seen earlier.” Security headers are exactly that. HSTS, Content-Security-Policy, X-Frame-Options, X-Content-Type-Options, and other headers are not exotic extras but standard requirements in many penetration tests and audits.
Therefore, we analyze every HTTP response for the presence and correctness of security-relevant headers. The trick is not the detection but the operationalization: missing or misconfigured headers are not reported as nebulous warnings but with concrete action recommendations, so the ops team or dev teams can follow up specifically.
For customers with increased requirements, additional checks can be added, such as automated checks along the OWASP Top 10 or OSINT analyses to detect forgotten subdomains, exposed information, or unintentionally public artifacts. The important thing is the positioning: these checks do not replace a pentest, but they reduce the likelihood that trivial findings only appear in the audit.
The shift from “reachable” to “observable” often begins with a simple metric: response time. We measure not only status codes but also latencies, TLS handshake duration, and—where sensible—response body validations. This allows degrading states to be recognized before slow becomes an outage.
In practice, this is one of the biggest levers for proactive operations: if response time histograms show that p95/p99 are continuously rising, it’s a signal, days before the incident. This enables countermeasures before the customer escalates.
Monitoring that only lives in its own UI creates new silos. Therefore, we export all monitoring data as Prometheus metrics. This allows them to be integrated into existing observability stacks like VictoriaMetrics and Grafana. For teams that have already established dashboards, this is a direct connection. For SLA customers, it is the basis for automated availability reports.
At this point, monitoring becomes reporting: availability, response time trends, error rates, and region comparisons can be depicted as dashboards and used as the basis for monthly SLA reports. Crucial: not manually from log files but automatically from metrics.
A good signal is of little use if the notification does not fit the operation. Therefore, we have established escalation paths that fit 24/7 organizations: notifications can go to the on-call technician, and if not acknowledged, to the team lead or a second on-call duty. Maintenance windows suppress alerts during planned work, and alert grouping combines related events instead of generating 50 individual messages.
The goal is not “more alerts,” but “the right alerts”—and in such a way that they are reliably processed in operation.
Another scaling lever was automatic endpoint discovery.
Wir helfen Ihnen, diesen Use Case auf Ihrer Infrastruktur zu realisieren – skalierbar, sicher und DSGVO-konform.
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