Unencoded URLs in email can pose subtle yet significant risks to email deliverability and spam filtering. While modern web browsers are often forgiving, automatically correcting malformed URLs, email systems (Mailbox Providers or MBPs) and spam filters are far less lenient. Their strict parsing and heuristic rules can flag such URLs as suspicious, potentially leading to messages being blocked or sent to the spam folder. This issue often arises when tracking parameters or dynamic content are appended to URLs without proper URL encoding, particularly when special characters like spaces or parentheses are included.
Key findings
Strict parsing: Unlike browsers, mailbox providers and spam filters may not automatically 'fix' unencoded URLs, treating them as malformed or suspicious.
Spamware indicator: Historically, poorly constructed URLs were a common sign of spam or malicious content, leading filters to be more sensitive to them.
SQL injection risk: Unencoded characters, especially keywords like 'update', 'delete', or 'select' in query parameters, can be misinterpreted as attempts at SQL injection or other nefarious activities, triggering security filters.
Desktop client issues: Some older or stricter desktop email clients (like Outlook) are particularly sensitive to malformed URLs and may flag them as scams or spam, even if MBPs do not.
Redirect and tracking impact: Even if the initial tracking URL is valid, if the final redirect URL is not properly encoded, it can lead to landing page errors, diminishing the user experience and potentially impacting engagement metrics.
Key considerations
URL encoding: Always ensure all components of a URL, especially query parameters containing special characters (like spaces or parentheses), are properly URL encoded. This includes data passed through ESP tracking links.
Naming conventions: Adopt naming schemes for UTM parameters or internal campaign identifiers that avoid spaces and special characters. Using hyphens or underscores can prevent encoding issues. For more on how links affect deliverability, consider our guide on HTTP tracking links.
ESP responsibility: Work with your Email Service Provider (ESP) to ensure their click-tracking and redirect mechanisms properly encode any dynamic parameters they append to your URLs. This is crucial for maintaining proper deliverability, especially when considering tracking URL subdomain alignment.
Testing: Thoroughly test email links across various email clients and devices to catch any encoding or rendering issues before sending to your entire list. For broader insights, see Do Links Hurt Email Deliverability?.
What email marketers say
Email marketers often discover unencoded URL issues when their campaigns experience unexpected problems, such as broken links or reduced inbox placement. While the immediate focus might be on user experience, the deeper concern lies in how these malformed URLs are perceived by spam filters and mailbox providers. Marketers frequently encounter situations where their tracking parameters, especially those automatically appended by their ESPs, contain characters that aren't properly encoded, leading to unpredictable deliverability outcomes and sometimes even landing page errors.
Key opinions
Browser forgiveness: Browsers are generally good at correcting malformed URLs, which can mask underlying encoding problems until a spam filter or specific email client encounters them.
ESP parameter issues: Many marketers find their email service provider's (ESP) click-tracking or redirect URLs are not properly encoding appended UTM or campaign parameters, especially those with spaces or parentheses.
Landing page errors: The primary indicator of a problem often surfaces as a landing page error, where the recipient's website doesn't correctly process the unencoded parameters.
Perceived security risk: Unencoded URLs, particularly those containing common database commands, can mistakenly be perceived by web application firewalls or other security measures as SQL injection attempts.
Information leakage: Marketers are concerned that unencoded campaign or segment names in URLs could expose internal marketing information to subscribers.
Key considerations
Proactive testing: Routinely check email links to ensure they render and redirect correctly across various email clients and web browsers before deployment. This is part of a broader email deliverability testing strategy.
Naming consistency: Implement strict internal guidelines for naming email campaigns and UTM parameters to avoid problematic characters. This can also prevent specific spam words from appearing unencoded.
ESP liaison: Communicate encoding requirements with your ESP to ensure their system handles all appended parameters correctly, reducing the risk of email deliverability issues and being flagged by a blacklist.
URL shorteners: While useful, be aware that URL shorteners can introduce their own deliverability considerations, as some can be associated with malicious activity. For further insights, Klaviyo offers advice on Email deliverability best practices related to email design.
Marketer view
Email marketer from Email Geeks indicates that their platform often appends query parameters with unencoded values like 'mailing name' (e.g., 'Foo Bar (1)'). They noted that browsers fix these automatically, so the issue often goes unnoticed until a server or strict filter complains.
19 Dec 2019 - Email Geeks
Marketer view
Email marketer from a Marketing Forum suggests that broken or malformed links, even if only at the landing page level, can significantly hurt user experience and overall campaign performance. It's not just about spam filters; it's about conversion too.
05 Nov 2023 - Marketing Forum
What the experts say
Email deliverability experts consistently advise against unencoded URLs, emphasizing the critical difference between how web browsers and mail processing agents (spam filters, antivirus, mailbox providers) interpret them. While a browser might silently correct a malformed URL, email infrastructure is designed to be highly suspicious of anything that deviates from strict standards, especially when it concerns links. This strictness is a defense mechanism against phishing, malware, and other malicious activities that often leverage malformed or obscure URLs. Experts highlight that unencoded special characters, or those that mimic SQL commands, can trigger advanced heuristics designed to protect recipients from sophisticated attacks.
Key opinions
Spamware heuristics: Poorly formatted URLs were a classic sign of spamware, leading many spam filters to still use such characteristics as a strong indicator for blocking.
Strict parsing by MBPs: Mailbox providers are much less forgiving than browsers. If a link won't load correctly because the URL is bad and their checking code doesn't fix it, it could be seen as an intentional attempt to bypass filters or lead to a non-existent page.
SQL injection similarity: Unencoded characters or phrases that resemble SQL statements (e.g., 'update', 'delete') within URL parameters can trigger security rules designed to prevent SQL injection attacks.
User click safety: There is a significant concern about what malicious actors can do once they convince a user to click a URL they control, or inject data into a legitimate service's URL, making strict URL validation crucial.
Desktop client quirks: Certain desktop email clients, notoriously Outlook, are known for their unusual handling of URLs, often quick to flag unencoded or strange links as scam or spam.
Key considerations
Strict adherence to RFCs: For optimal deliverability, URLs must strictly adhere to RFC specifications regarding encoding. Any deviation increases the risk of filtering. See our article on what RFC 5322 says vs. what actually works.
Preventing security flags: Proactive URL encoding helps prevent emails from being flagged for potential SQL injection or other web-based vulnerabilities, which can severely impact sender reputation and lead to blacklisting (or blocklisting).
Consistent URL structure: Standardize URL structures and parameter naming to avoid characters that require encoding. This simplifies parsing for email systems and reduces the chance of misinterpretation.
Impact on engagement: Even if an email lands in the inbox, a broken or suspicious-looking link will deter clicks and harm overall engagement. Monitoring engagement is key to understanding how links affect deliverability.
Expert view
Deliverability expert from Email Geeks suggests that older heuristics might flag badly formed URLs within the message body as a sign of spamware. However, they indicate that systems checking for malicious content by clicking through are less likely to use this heuristic.
19 Dec 2019 - Email Geeks
Expert view
Expert from SpamResource highlights that any element that deviates from standard email formatting or common web protocols can be seen as suspicious by advanced spam filters. Unencoded URLs fall squarely into this category, potentially impacting inbox placement.
20 May 2024 - SpamResource
What the documentation says
Official documentation from various internet standards bodies (RFCs) and mailbox providers consistently advocates for strict adherence to URL encoding guidelines. These guidelines are fundamental to the interoperability and security of the internet. Unencoded URLs violate these standards, making them unpredictable in how they are processed by diverse email systems and increasing their likelihood of being flagged as non-compliant or malicious. Documentation often warns that while browsers might be tolerant, server-side processing and security systems are not, and will often reject malformed requests or interpret them as threats, impacting both deliverability and website functionality.
Key findings
RFC compliance: RFC 3986, the Uniform Resource Identifier (URI) Generic Syntax, specifies that certain characters (like spaces) must be percent-encoded when used in URIs to avoid ambiguity.
Security vulnerability: Unencoded characters, especially those used in scripting or SQL, can be interpreted as code injection attempts by web application firewalls and email security gateways.
Interoperability issues: Disregarding URL encoding standards can lead to links breaking or behaving inconsistently across different email clients, operating systems, and network configurations.
Spam score contribution: Many spam filtering engines (e.g., SpamAssassin) assign penalty scores for non-standard URL formatting, including the presence of unencoded spaces or problematic characters.
Malicious content association: Unusual or malformed URLs are a common characteristic of phishing attempts and malware distribution, leading security systems to treat them with high suspicion.
Key considerations
Automated encoding: Ensure your email sending platform or custom application automatically applies proper URL encoding to all dynamic parameters and entire URLs. This is a critical technical solution for boosting email deliverability rates.
URL canonicalization: Maintain consistent and canonical forms of your URLs in emails. Avoid variations that could be subject to misinterpretation or incomplete encoding.
Compliance with major providers: Review guidelines from major mailbox providers (Google, Yahoo, Microsoft) regarding link formatting. Many have specific recommendations to prevent filtering. You can find out more about Outlook's new sender requirements.
Use of HTTPS/SSL: While not directly related to encoding, always using HTTPS for links ensures secure data transmission and builds trust, indirectly reinforcing positive sender reputation and potentially assisting with how links are viewed by filters. Consult our resource on using HTTPS/SSL for email links.
Technical article
RFC 3986 (URI Generic Syntax) dictates that Uniform Resource Identifiers (URIs) must strictly adhere to specific syntax rules. Characters outside of the unreserved set must be percent-encoded to prevent misinterpretation and ensure global interoperability across various systems.
Jan 2005 - RFC 3986
Technical article
The OWASP (Open Web Application Security Project) documentation on URL encoding notes that improper encoding or decoding of URL parameters is a common vector for web vulnerabilities, including SQL injection and cross-site scripting (XSS) attacks. Security systems are designed to detect these anomalies.