How should security teams train users to spot phishing URLs before they click?

Why URL training works when users learn to read the right part of the link

Phishing URL training is most effective when users are taught a simple parsing habit: identify the registrable domain first, then treat everything before it as potentially deceptive decoration. Attackers rely on visual shortcuts, especially when they place a trusted brand name in a subdomain or path and make the actual destination easy to miss. Training should make that mismatch obvious.

The practical goal is not to turn every employee into a URL parser, but to slow down the exact click decision. Users only need enough structure to spot lookalikes, odd protocol switches, and hostname chains that borrow trust from familiar names. That makes the lesson repeatable, testable, and more durable than a list of suspicious keywords.

Security teams can reinforce this with examples that contrast the visible text with the actual destination. For example, a link can appear to point to a well-known service while the real domain is unrelated, or a subdomain can contain a brand name while the registrable domain belongs to an attacker. That is why right-to-left reading is more reliable than reading left-to-right for trust judgment.

When users also see how URL structure connects to account compromise, the lesson becomes more memorable. A phishing page is only dangerous if it successfully captures credentials, tokens, or session data, so the review habit should be tied to the moment before submission, not just the moment before clicking. Internal case studies such as MailChimp Breach and CoPhish OAuth Token Theft via Copilot Studio illustrate how social engineering and token theft turn a single bad click into broader access.

A useful training metric is whether users can explain what makes a URL real, not whether they can recite an abstract warning. If they can identify the second-level domain, spot a misleading subdomain, and notice a protocol or hostname that does not fit the expected service, the training is doing its job. If they cannot do that quickly, the material is too generic.

Common URL patterns that deserve extra suspicion

Most users do not need every possible phishing trick. They need to recognise a small set of patterns that repeatedly show up in lookalike URLs. Misspellings, digits inserted into brand names, extra hyphens, and long chains of subdomains are all designed to exploit hurried reading. So are unusual protocols or links that redirect through several hops before landing on the final page.

Teams should also teach users to distrust domains that look almost right but are not the exact registrable domain they expect. The attack is often not technical sophistication, but presentation, the attacker wants the URL to be believable at a glance. This is why training should compare “looks like the brand” with “is actually the brand’s domain” and make the gap visually obvious.

Well-designed drills should include both obvious and subtle examples. Obvious examples help establish the rule. Subtle examples build the habit of checking the part of the URL that actually controls destination. If the training never uses realistic edge cases, users may perform well in the classroom and fail in the inbox.

One useful supporting reference is NIST SP 800-63 Digital Identity Guidelines, because phishing-resistant authentication only helps after the user avoids handing over credentials in the first place. For organisations that want broader control coverage, NIST SP 800-53 Rev 5 Security and Privacy Controls and OWASP API Security Top 10 are useful complements for reinforcing access control and limiting blast radius after a credential capture.

Where phishing awareness is paired with incident response practice, teams can also use FIRST guidance to keep reporting paths clear when users spot a suspicious link before or after a click. That shortens the time between detection and containment.

Practitioner Guidance

What to prioritise: Teach the URL check as a fast, repeatable pre-click habit. The most useful lesson is not “be careful,” but “read the registrable domain first and ignore branding noise in subdomains, paths, and redirects.”

What to verify: Validate that users can perform the check under time pressure. A good test is whether they can explain why two URLs differ in destination even when both contain the same brand name somewhere in the string.

Common mistake: Do not rely on awareness slides that only show obviously broken examples. Real phishing URLs often look locally plausible, so training must include close lookalikes, mixed subdomains, and typo variants that force deliberate reading.

Practitioner takeaway: Effective phishing URL training changes user behaviour at the point of decision, not just their vocabulary. If the user can slow down, isolate the real domain, and ignore decorative brand text, the control has a chance to work.

Related resources from NHI Mgmt Group

• How should security teams detect phishing before users click malicious links or decode QR codes?
• How should security teams detect homoglyph phishing domains before users click them?
• How should security teams train users when phishing emails are AI-generated?
• How should security teams train users for phishing, vishing, and smishing together?