How Link Shorteners Can Hurt Deliverability

Why Link Shorteners Can Hurt Email Deliverability

Link shorteners became popular because they transform long web addresses into shorter links. They are useful for sharing URLs on social media, tracking clicks, and making printed or digital messages easier to read.

However, their use in email marketing can create deliverability risks. Services such as Bitly allow users to share shortened links that redirect to another destination. Although the technology is legitimate, the same mechanism can be abused to hide phishing pages, fraudulent websites, and other malicious destinations.

Email security systems therefore examine links and redirects to evaluate the destination and associated risks. Amazon Web Services recommends avoiding generic link shorteners in email campaigns, and Twilio SendGrid explains that shared shortening domains may be associated with abuse.

There are several reasons why this matters.

10.1 Shared domain reputation

When many unrelated people use the same shortening domain, one sender’s behavior may contribute to the domain’s reputation problems.

If a shortening service is abused by malicious senders, some security systems may block or distrust links from that service. A legitimate business using the same domain could then experience problems even when its own website is safe.

This does not mean every shortened link is blocked. The risk depends on the shortening service, its reputation, the destination, and the receiving provider’s filtering policies.

10.2 Hidden destinations reduce trust

Consider two links:

• https://example.com/resources/email-guide

• https://short.example/Ab12Cd

The first clearly identifies the destination. The second does not reveal where the recipient will be redirected.

Recipients may hesitate to click unfamiliar shortened links, particularly in cold outreach emails from people they do not know. Security filters may also inspect the redirect before deciding whether to accept or deliver the message.

Google’s sender guidance recommends that email links be clear and easy to understand so recipients know what to expect.

10.3 Multiple redirects complicate security checks

A shortened URL may redirect through several domains before reaching the final webpage.

Each additional step can introduce uncertainty. A destination may change, a tracking service may malfunction, or a domain in the redirect chain may have a poor reputation.

For example, a link might pass through a public shortener, a click-tracking service, and a landing-page redirect before reaching the final website.

Security systems may inspect each stage, and a suspicious domain anywhere in the chain can contribute to a rejection or warning.

10.4 Tracking practices can create unnecessary risk

Some email platforms rewrite links to record clicks. This can be legitimate and useful for campaign reporting, but it adds another domain and redirect to the message.

If tracking domains are poorly configured, unfamiliar, or associated with suspicious activity, they may create additional deliverability concerns.

Businesses should therefore use reputable email service providers, configure custom tracking domains when supported, and test how rewritten links resolve.

10.5 Shorteners can reduce recipient confidence

Deliverability is not determined by link structure alone. Recipient behavior also matters.

A prospect who receives an unexpected email containing several unfamiliar shortened links may be less willing to engage with the message. They might delete it or report it as spam.

For cold outreach, this can be especially damaging because the recipient has not yet developed trust in the sender. In newsletters, unexplained shortened links can make a familiar brand appear less transparent.

The most effective approach is to make the destination understandable and ensure that every link supports the email’s stated purpose.

11. Case Study: How Link Shorteners Affected a Company’s Email Deliverability

The following case study is hypothetical and is intended to illustrate how a business might diagnose and address link-related deliverability problems. The figures are illustrative, not independently verified results.

Background

BrightWave Marketing is a fictional digital marketing agency that provides email marketing, website development, and lead generation services to small and medium-sized businesses.

The company operates two email programs. Its sales team sends cold outreach messages to potential clients, while its marketing team distributes a weekly newsletter to subscribers.

Initially, both teams used public URL shorteners to make links look cleaner and to track clicks. The sales team included shortened links to service pages and booking forms. The newsletter team used shortened links for blog articles, product updates, and promotional offers.

After several weeks, the company noticed a decline in email performance. Fewer prospects were responding, newsletter clicks were decreasing, and some campaigns showed signs of increased filtering.

The team initially suspected that its subject lines were ineffective. However, after reviewing campaign reports, it decided to investigate the links included in its messages.

The problems identified

The investigation identified four potential problems.

First, the team relied heavily on a shared shortening domain. Because the service was used by many unrelated senders, the company had limited control over its reputation.

Second, recipients could not easily identify the final destinations. Some prospects were reluctant to click unfamiliar links from a company they had never contacted before.

Third, several messages contained unnecessary redirects. The shortening service forwarded users to a tracking link, which then forwarded them to the agency’s website.

Fourth, the company had insufficient link testing procedures. The marketing team did not consistently check redirect destinations, mobile compatibility, or expired landing pages before sending campaigns.

These findings suggested that link practices could be contributing to the problem. However, the company recognized that link shorteners were not necessarily the sole cause. Sender reputation, recipient engagement, list quality, authentication, and message content could also affect delivery.

Step 1: Replace unnecessary public short links

BrightWave removed generic shortened links from its cold outreach templates.

Instead of sending a prospect to an unfamiliar short URL, the sales team used a clear link to a relevant page on the company’s website.

For example, a message could include the descriptive text “View our email marketing services” linked directly to the appropriate company page.

The team also reduced the number of links in initial outreach emails. Each link had a clear purpose, and the email explained what the recipient would find after clicking.

Step 2: Review tracking infrastructure

The marketing team examined the click-tracking configuration provided by its email service provider.

Where supported, it configured a branded tracking domain and checked that the domain resolved correctly. It also reviewed the redirect chain to remove unnecessary steps.

The company did not assume that branded tracking automatically guaranteed inbox placement. Instead, it treated the configuration as one element of a broader deliverability improvement program.

Step 3: Test links before sending

BrightWave introduced a pre-send checklist requiring staff to verify every destination.

The checklist included:

• Confirming that each URL reaches the intended webpage.

• Checking that the destination uses HTTPS where appropriate.

• Removing broken, expired, or irrelevant links.

• Testing pages on desktop and mobile devices.

• Reviewing redirects for unexpected or unnecessary domains.

• Ensuring that the visible link text accurately describes the destination.

The team also checked whether landing pages contained useful information consistent with the email’s claims.

Step 4: Monitor results and investigate other causes

The company reviewed its email authentication, bounce rates, spam complaints, and sending patterns alongside its link changes.

It compared campaigns with similar audiences and purposes rather than assuming that a single improvement explained every result.

It also reviewed its prospecting practices and removed invalid contacts from its outreach list.

Illustrative results

After six weeks, BrightWave compared selected metrics before and after its changes.

These hypothetical results illustrate a possible improvement following a combination of link cleanup, list maintenance, and better campaign practices. They do not prove that removing shorteners alone produced the changes.

The company would need controlled testing and additional data to determine the independent effect of each intervention.

Lessons learned

The first lesson is that a shorter URL is not necessarily a better URL. A descriptive, trustworthy destination may be more valuable than a link that simply looks compact.

The second lesson is that the final destination matters. A legitimate-looking short link cannot compensate for a suspicious, broken, or misleading landing page.

The third lesson is that tracking should be implemented carefully. Click measurement is useful, but unnecessary redirects create additional complexity.

Finally, deliverability improvements require a comprehensive approach. Link management should be considered alongside authentication, list quality, recipient relevance, and complaint monitoring.

12. Best Practices for Using Links Without Hurting Deliverability

Businesses can reduce avoidable link-related risks by following these practices.

Use direct links whenever practical

Whenever possible, link directly to the intended webpage on a domain your organization controls. This makes the destination easier to recognize and reduces the need for unnecessary redirects.

Prefer branded short links when shortening is necessary

If a short URL is genuinely useful, consider a custom domain associated with your organization rather than a generic, shared shortening service.

A branded short link can improve recognizability, but it does not guarantee good deliverability. The destination and reputation of the domain still matter.

Limit unnecessary links

Cold outreach messages generally benefit from a clear purpose and a simple next step. A prospecting email that contains several links to unrelated pages can appear overly promotional.

Newsletters may naturally contain multiple links, but each should serve the reader. Include relevant article links, clear calls to action, and required subscription-management links.

Test every destination

Test links before each major campaign, especially when URLs have been changed or tracking settings have been updated.

Make sure links reach the intended pages and that recipients are not unexpectedly redirected to unrelated websites.

Monitor sender and domain reputation

Use available provider tools, email service provider reports, and delivery logs to investigate unusual rejection patterns.

For Gmail, Google Postmaster Tools can help eligible senders monitor domain and IP reputation, spam rates, and other delivery signals. See the Google Postmaster Tools documentation.

Remember that reputation indicators do not identify every cause of a filtering problem. Combine them with message testing and campaign-level analysis.

Avoid misleading link text

The visible wording of a link should accurately represent its destination. Do not disguise a suspicious domain behind reassuring text or send recipients to a destination unrelated to the message.

Transparency benefits recipients and helps maintain confidence in your communications.

13. When Should You Avoid Link Shorteners Completely?

Avoid public shortening services when sending cold outreach to unfamiliar prospects if the shortener provides no meaningful benefit.

You should also avoid them when:

• The receiving provider or your email service provider discourages their use.

• The destination is unfamiliar or cannot be verified.

• The redirect chain is unnecessarily long.

• You have recently experienced link-related filtering or rejection.

• Your message contains several unrelated shortened URLs.

• You cannot control or monitor the final destination.

  14. The Historical Turning Point: Why Email Providers Became More Careful About Links

  One of the clearest examples of how the relationship between link shorteners and trust developed is the guidance published by email delivery providers.

  In September 2013, SendGrid published an article explaining why public URL shorteners could be problematic in email. The article highlighted the fact that spammers used shortening services to conceal their destinations, potentially exposing legitimate senders to filtering problems.

  

  SendGrid

  This illustrates an important historical change. URL shortening began as a convenience, but it became a security concern as the internet faced increasing abuse.

  Another milestone came with Google’s changing approach to its own URL-shortening service. Google announced the deprecation of its URL Shortener in 2018 and subsequently announced that most remaining goo.gl links would stop working after August 25, 2025, while certain links created through Google products would continue to function.

  

  Google Developers Blog

  This development highlighted a second risk: link permanence and control. If a business relies on a third-party service for important campaign links, it depends on that provider’s continued operation and policies.

  For email marketers, the historical lesson is twofold. First, shortening a URL does not remove the need to establish trust. Second, businesses should understand who controls their links and what happens if a shortening service changes its policies or discontinues its service.

  15. The Role of Spam Filters in the Modern History of Link Shorteners

  As email security improved, filtering systems increasingly examined multiple characteristics of a message rather than relying on a single spam keyword or formatting rule.

  Links became one part of this broader evaluation. Receiving systems could assess the domain, redirect behavior, destination reputation, and consistency between the apparent purpose of an email and the website it promoted.

  The Google email sender guidelines specifically advise that links in message bodies should be visible and easy to understand, so recipients know what to expect when they click. The guidelines also emphasize accurate sender information and responsible sending practices.

  

  Gmail Help

  This guidance reflects years of experience with phishing, deceptive messages, and unwanted email.

  Why this matters for deliverability

  Consider a business that sends a legitimate newsletter containing a shortened link to an educational article. The destination may be completely safe, but the recipient cannot easily determine where the link leads.

  A security system may examine the destination and allow the message through. Another system may evaluate the shortening domain’s reputation or the complete redirect chain differently.

  Therefore, a shortened link does not automatically cause a message to enter spam. Its effect depends on several factors, including the provider’s filtering system, the reputation of the domains involved, and the overall characteristics of the email.

  This distinction is important because businesses sometimes blame a single link for a deliverability decline without investigating other possible causes.

  Historically, deliverability management has progressed from simple assumptions about message content toward a broader evaluation of sender identity, domain reputation, recipient behavior, and link safety.

  16. The Evolution of Link Shorteners in Cold Outreach

  Cold outreach has been particularly affected by changing attitudes toward shortened links.

  In the early days of business email, marketers often emphasized reaching as many prospects as possible. Shortened URLs offered a convenient way to share product pages, booking forms, and promotional resources.

  As unwanted email increased, however, recipients became more cautious about clicking unfamiliar links.

  A shortened link in an unsolicited message can create uncertainty because the recipient may not recognize either the sender or the destination.

  From mass messaging to relevant communication

  Modern cold outreach increasingly emphasizes relevance, transparency, and professional credibility.

  For example, a consultant contacting a potential client might write:

  “Here is our guide to improving email campaign performance.”

  A direct link to the consultant’s website allows the recipient to recognize the destination before clicking.

  By contrast, a generic shortened URL provides less information about where the recipient will go.

  The direct link does not guarantee inbox placement, but it removes an unnecessary source of uncertainty.

  The development of branded tracking domains

  As campaign analytics became more sophisticated, marketers sought ways to measure clicks without relying entirely on generic shortening services.

  Branded tracking domains emerged as one option. These domains can provide a recognizable link associated with the sender’s organization while supporting click measurement.

  However, branding is not a complete solution. A branded tracking domain can still develop a poor reputation if it is misused, redirects visitors to harmful destinations, or is configured insecurely.

  The historical lesson is that control and accountability matter more than the appearance of a short URL.

  For cold outreach, the most appropriate approach is generally to use relevant links sparingly, prefer recognizable destinations, and ensure that any tracking system is configured responsibly.

  17. The Evolution of Link Shorteners in Newsletter Marketing

  Newsletter marketing has followed a somewhat different path.

  Publishers and businesses often distribute several articles, product announcements, and calls to action in one email. They may therefore have legitimate reasons to track clicks and measure the performance of individual links.

  Shorteners and tracking systems have helped marketers understand which content attracts attention. However, these tools have also introduced technical dependencies and additional redirect steps.

  From basic newsletters to measurable campaigns

  Early newsletters were primarily concerned with distributing information. As email marketing platforms developed, marketers gained more sophisticated campaign analytics.

  They could measure clicks, compare content performance, and identify which links generated meaningful engagement.

  These capabilities helped newsletter teams make better editorial and commercial decisions. Nevertheless, the desire to measure every click sometimes resulted in unnecessarily complicated tracking arrangements.

  For example, a link might pass through a public shortener, a campaign tracking system, and a separate landing-page redirect before reaching the intended article.

  Each additional step creates another point where a technical failure, reputation concern, or destination change may affect the recipient’s experience.

  The modern newsletter approach

  Today, newsletter publishers can often use their email service provider’s built-in click tracking or a branded tracking domain.

  They should still test the complete redirect path and verify that the final destination is appropriate.

  It is also important to interpret campaign results carefully. A decline in newsletter clicks may reflect less relevant content, changes in subscriber behavior, broken links, or other factors. It does not necessarily mean that a shortening domain has damaged deliverability.

  The historical lesson is that tracking should support the reader’s experience rather than complicate it.

  18. What the History Teaches Businesses Today

  The development of link shorteners offers several practical lessons for businesses that depend on email.

  First, convenience can introduce hidden dependencies. A shortened URL may look cleaner, but it depends on a redirect service that must remain operational and trustworthy.

  Second, transparency builds confidence. Recognizable destinations help recipients understand what they are being asked to click.

  Third, reputation is not entirely under the sender’s control. A public shortener may be shared by many unrelated users. Their activity can affect how some security systems perceive the shared domain.

  Fourth, link management is part of a larger deliverability strategy. Authentication, recipient relevance, list quality, complaint rates, and sending behavior remain essential.

  Fifth, problems should be diagnosed rather than assumed. When deliverability declines, businesses should examine bounce logs, provider responses, authentication results, domain reputation, and redirect behavior before deciding that shortened links are responsible.

  These lessons apply to both cold outreach and newsletters, even though the two programs serve different purposes.

  Conclusion

  The history of how link shorteners can hurt deliverability reflects the wider evolution of email from a convenient communication tool into a security-sensitive marketing channel.

  URL shortening emerged to solve a practical problem: making long web addresses easier to share. As its use expanded, however, malicious actors began exploiting the same technology to hide suspicious destinations. This created challenges for recipients, security systems, and legitimate email senders.

  Over time, email providers increasingly emphasized trustworthy sender identity, understandable links, and responsible sending behavior. The experience of services such as SendGrid and the retirement of Google’s URL Shortener demonstrate why businesses must consider both the reputation and long-term reliability of their link infrastructure.

  For cold outreach, direct and relevant links can help establish credibility with unfamiliar recipients. For newsletters, carefully configured tracking and recognizable destinations can support analytics without unnecessarily complicating the reader’s experience.

  Ultimately, link shorteners are not inherently harmful, and their presence does not automatically send an email to spam. Their impact depends on the service, its reputation, the redirect chain, the destination, and the wider context of the message.