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How to Fix Outlook Deliverability Issues
7 min read

How to Fix Outlook Deliverability Issues

How to Fix Outlook Deliverability Issues

When it comes to engaging with subscribers, contacts, prospects, or customers, one of the main tools used by both professionals and regular people is the email client developed by Microsoft. Of course, we are talking about Outlook, the software included in the Office 365 package, one of the must-have enterprise software on the market. But how can marketers, entrepreneurs, and sales executives make sure they are following best practices and that their email communication is actually reaching the inboxes of their contacts?

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Furthermore, if we consider that the web-based Outlook mailbox is gaining more popularity, being currently the third most used email client on the market, looking into how to fix Outlook deliverability issues could be a timely topic. In this article, we are going to go over best practices and tips and tricks for sending out email communication to Outlook mailboxes.


Outlook deliverability issues

The first and most important aspect that you need to understand when trying to figure out how to send emails in Outlook inboxes is the filters Microsoft uses to determine legitimate communication from spam or unsolicited email. Here you would deal with two main filters:

  • Exchange Online Protection
    This filter applies by investigating deliverability-sensitive aspects such as sender reputation and sender IP. It does not take the actual content of an email into account when deciding how to deal with each individual correspondence.
  • Smart Screen
    This filter is aimed at analyzing both the technical aspects of email deliverability, such as the ones we have mentioned above, but it also looks at content and engagement. Therefore, the Smart Screen might affect emails sent from reputable sources, but that have a low engagement or contain sensitive topics or keywords.

The good news about these filters is that Microsoft is very transparent with businesses regarding this data for Outlook.com mailboxes. By joining the Smart Network Data Services, companies can request data that will help them improve their sender reputation and good standing with Outlook. If you haven’t done that yet, you should create an account and get started with work that will positively impact the chances of sending emails directly to Outlook inboxes.


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Email deliverability best practices

Of course, reaching the inbox is not just a technical challenge, it is also the result of a relationship you build and maintain with your subscribers. Even if we do not look at Outlook deliverability issues in particular, knowing and following the industry best practices is one of the most jobs an email marketer or sales representative needs to do. That’s why we will go over these best practices together.

  • Authenticate emails

Even before starting to send out emails, you need to make sure that you have authenticated all emails using DMARC, DKIM, and SPF. That’s how you communicate to the server that the email you will be sending out is legitimate, associated with a certain domain and IP as well as the fact that the sender email is real. If you haven’t done that yet or if you are not sure about the status of your email authentication, take some time to check that out. Any issues you might encounter will be fixed easily and your overall reputation will increase.

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  • Always use a reputable ESP

When it comes to email service providers there are so many tools at your disposal. But be wary of choosing an ESP that might charge less but doesn’t focus on following deliverability best practices or one that is associated with sending out spam. You don’t want all your hard work to be negatively impacted by other companies or individuals using the same ESP for shady practices. Go for a company that you can find reviews for online, one that is transparent with how it deals with spam and one that you can easily contact if you run into any kind of problems.

  • Clean up your email lists

This is probably the easiest thing to implement. Not just the easiest, but the one thing that you can do that will result in the most beneficial outcomes for your overall sender reputation. DataValidation offers an email verification solution that can help businesses large and small with maintaining clean email lists. Our long-standing experience in the market shows that companies that verify their email lists on a monthly basis have seen increases in terms of engagement, deliverability, and even ROI. Do not hesitate and try out our service. For each list that you upload or import into the DataValidation app, you will receive a free quality report, that will indicate the grades for those specific contacts.

  • Validate URLs

Make sure that all URLs included in the email are valid, that subscribers will be able to access them. Furthermore, never include short URLs in an email.

  • Pay attention to attachments

Depending on the type of email you are sending out, attachments might be something that you will have to include. While having links to those files stored in the cloud, with Google Drive or One Drive is always the best approach if you absolutely have to attach a document to an email, then make sure it doesn’t have more than 25 MB or your email will not get in the subscriber’s inbox.

  • Keep the email clean

This takes us back to the point about picking an ESP. Never include scripts in your email. JavaScript or ActiveX scripts are a clear no-no when it comes to designing an email.

  • Avoid spam-like practices

This is a no-brainer, but we need to mention it here. Do not engage in spam-like practices. Do not purchase email lists. Do not send out unsolicited emails. Do not send emails about sensitive topics that most spam filters will block (adult content, pharmaceutical, loans). Never do anything illegal when sending out emails (phishing attempts, sending out malware, or ransomware). Always include an unsubscribing option in the email and follow-through with any such requests. Do not use misleading subject lines or outright false advertising in your emails.

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Be very careful when designing an email. Even if you avoid doing any of the things we have listed above, if you are placing too many CTA buttons or the text is barely visible or if your emails are not responsive, you might still be exposing yourself to deliverability issues.

  • Build a relationship

If you have a clear schedule for sending out emails, stick to it. If you don’t, try to implement a calendar. You want your subscribers to know what to expect from you. If you are able to build and maintain that relationship, you can also encourage them to add your email address to their contacts. Doing so will almost guarantee that your emails will reach the inbox every time, as long as you follow all the best practices we have talked about already.


Contacting Microsoft

If you have noticed any kind of deliverability issues with Outlook, you have the option of contacting Microsoft. Only do that after you have made sure that all the guidelines we have discussed in this article are being met. Do not expect any miracle from addressing the issue with Microsoft directly. Email deliverability issues will result in hard work on your part, even if you get an answer from Microsoft about what needs to be fixed. Always use the contact option as a last resort, after you have checked that you are compliant not just with best practices, but will legal requirements and specific conditions that Outlook has.

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The best approach to improving Outlook deliverability is by following the rules. Circumventing them might sound appealing at first or you just might not have the time to do all the work, but being locked out from sending out emails will most likely have a bigger financial impact, without talking about how it will damage your brand.