How to Schedule an Email in Outlook Without Limitations

Scheduling emails should be simple, but in Outlook, it often feels like a chore. The built-in “Delay Delivery” option is tucked away in menus, only works if your device stays online, and doesn’t allow you to set up recurring sends or campaigns. For internal communicators, HR teams, and leaders who need to plan announcements, reminders, or newsletters in advance, these limitations quickly add up.

At the same time, timing has never been more important. The DMA/Marigold Email Benchmarking Report 2025 supports the fact that “email continues to be one of the most personal, powerful ways to connect.” The report also shows that all four core metrics — opens, clicks, click-to-opens, and deliverability — are trending upward, underscoring the opportunity when emails are delivered effectively. 

But rising engagement metrics don’t tell the full story. Without considering when emails land, the flood of workplace messages can quickly drown out even the most carefully crafted communication.

A 2025 Microsoft Work Trend Index Special Report warns of the “infinite workday,” where employees are flooded with nonstop messages, often checking inboxes before sunrise and struggling to keep up. It talks about:

• A workday that often begins before lots of people have even gotten out of bed. 
• The chaos of the infinite workday that “starts early, mostly in email, and quickly swells to a focus-sapping flood of messages, meetings, and interruptions”.
• An infinite workday that “bleeds into evenings and weekends”.

“The inbox may still be the front door to work, but too often it opens to a flood of unprioritized chaos.” Microsoft

While quite different from one another, the findings of these two reports highlight a growing truth. Without smarter scheduling tools, even the most important updates risk being buried in overload.

Scheduling emails is the key, but it only works with the right tools.

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How to Schedule Email Outlook

For many years, Microsoft has been encouraging users to schedule emails using Outlook’s Schedule Send feature to improve productivity. For instance, just a couple of years ago, they stated in an online post, “Life gets busy—and you don’t always have time to sit down and send an email. But what if you could write an email when you have some extra time—and send it later without even lifting a finger?” The message was, “Set it and forget it.”

Outlook does provide scheduling options, but how you use them depends on the version you’re working in. Microsoft has built slightly different processes for the New Outlook, Classic Outlook, and Outlook on the Web. While the steps are fairly straightforward, each comes with its own quirks and limitations that communicators should be aware of before relying on them. 

We’re going to walk through how to schedule an email in Outlook in each of the three environments.

How to Schedule an Email in New Outlook

If you’re using the New Outlook, available for Microsoft 365 and Outlook.com accounts, you can schedule emails with the Send later feature. To do this:

1. Open a new message.
2. Select Send later (found next to the Send button).
3. Choose the desired date and time for delivery.

Once set, your email will automatically send at the scheduled time. 

However, this feature only works for Microsoft 365 and Outlook.com accounts. It doesn’t support IMAP or POP accounts. Many users discover this limitation only after attempting to schedule, which can create confusion or missed sends.

How to Schedule an Email in Classic Outlook

In the Classic Outlook desktop app, scheduling emails involves the Delay Delivery option. Here’s how it works:

1. Compose a new email.
2. Go to the Options tab and select Delay Delivery.
3. Under “Delivery options,” check Do not deliver before and select your desired date and time.

Your message will then stay in the Outbox until it’s time to send. 

One important caveat is that Classic Outlook requires the app to remain open and connected to the internet at the scheduled time. If your computer is turned off, asleep, or offline, the email won’t be sent until Outlook is running again.

How to Schedule an Email in Outlook on the Web or Outlook.com

For Outlook on the Web and Outlook.com, scheduling is a bit more seamless. You can queue messages in the cloud without relying on your device:

1. Compose a new email.
2. Click the dropdown arrow next to Send and select Send later.
3. Pick the date and time you want the email delivered, then confirm.

Because these versions run on Microsoft’s cloud, your computer doesn’t need to stay online. Once scheduled, the message will be delivered at your chosen time automatically. This makes it a more reliable option compared to Classic Outlook, though still limited to scheduling one-off emails.

Limitations of Outlook Email Scheduling

While Outlook offers ways to delay or schedule emails across its different versions, the functionality is far from robust. The features are often hidden, inconsistent between platforms, and lack the flexibility that internal communicators, HR teams, and leaders need to manage campaigns effectively. Beyond the basics, Outlook doesn’t support recurring sends, coordinated campaigns, or any performance insights. 

Here are the five key limitations to be aware of:

#1 Clunky Workflow

The scheduling tools in Outlook are not intuitive. In Classic Outlook, “Delay Delivery” is not intuitive. Instead, it is buried under multiple menus, making it easy for users to overlook or misconfigure. Even in the New Outlook and Outlook on the Web, the process can feel like an afterthought rather than a well-integrated feature. This creates friction for communicators who need to schedule emails quickly and reliably.

#2 No Campaign/Weekly Scheduling

Outlook only allows users to schedule individual messages. If you want to send a recurring update, such as a weekly newsletter, monthly compliance reminder, or quarterly leadership message, you’ll need to manually schedule each one. There’s no way to automate recurring campaigns, which means more manual work and greater risk of errors or missed deadlines.

#3 Dependent on Your Device Being Online

In Classic Outlook, scheduled emails sit in the Outbox until they’re released at the chosen time. But if Outlook isn’t open and connected to the internet at that moment, the email won’t send. This limitation is particularly risky for teams working across time zones or scheduling important messages outside of office hours. By contrast, cloud-based scheduling (like in Outlook on the Web) eliminates this issue, but only for certain accounts.

#4 Restrictions in the New Outlook

The New Outlook does provide a “Send later” option, but it’s not available for all account types. IMAP and POP accounts aren’t supported, leaving many users frustrated when they realize scheduling simply isn’t an option. 

Microsoft’s own forums are filled with complaints from users reporting that “Schedule send” is missing or unavailable in the New Outlook interface. These inconsistencies make the feature unreliable across different environments.

Many users are complaining that the schedule send feature is missing or is not an option anymore. 

#5 No Analytics

Even if your email is scheduled and delivered successfully, Outlook doesn’t provide any performance data. There are no metrics on open rates, click-throughs, or acknowledgments — all insights that are critical for internal communicators to measure effectiveness. Without analytics, it’s impossible to know whether employees saw or engaged with your message, making it harder to refine communication strategies or prove impact.

Why Email Scheduling Matters for Internal Communicators

For internal communicators, HR teams, and business leaders, sending an email isn’t just about hitting “Send.” It’s about ensuring that the right message reaches employees at the right moment. The limitations in Outlook’s scheduling tools highlight why more reliable options are necessary.

Patrick Wyllie, President at 32One Media, published a post on the topic on LinkedIn. Why You Should Schedule Send Emails that talks about the benefit of scheduling email sends. He highlights:

• Enhanced productivity
• Improving email effectiveness
• Respecting recipients’ boundaries
• Encouraging healthy work habits

Our approach is a little different, but we’re speaking the same language.

“The simple act of scheduling an email to send later is more than just a tool for clearing your own plate; it's a step towards cultivating a more balanced, respectful, and productive work environment. As we continue to navigate the complexities of work-life balance in the digital age, embracing technologies and practices that support this balance is not just beneficial—it's essential.” Patrick Wyllie 

Employee Engagement Depends on Timing

Employees are far more likely to engage with communications when messages arrive at a moment that fits naturally into their workday. A well-timed email can boost open rates, encourage clicks, and make important updates stand out amid the noise of daily notifications. Poorly timed emails, on the other hand, risk being ignored or buried.

Reducing Email Overload

Most employees already face inbox fatigue. By scheduling messages strategically, communicators can pace announcements to avoid overwhelming staff. Instead of receiving multiple updates all at once, employees can engage with information in a steady, manageable flow.

Supporting Campaign Planning

Internal campaigns like compliance training, benefits enrollment, or wellness initiatives depend on consistent communication. Scheduling ensures that key reminders go out on time, every time. Without it, campaign timelines are vulnerable to human error, rushed messaging, or inconsistent delivery.

Meeting Deadlines Across Time Zones

In today’s global organizations, employees often work across different regions. Scheduling tools allow communicators to plan sends in advance and ensure delivery aligns with employees’ local working hours, rather than the sender’s. This makes communication more relevant and respectful of work-life balance.

Building Trust in Communication Channels

When employees consistently receive clear, timely updates, they learn to rely on internal email as a dependable channel. Without reliable scheduling, however, organizations risk undermining trust — especially if critical messages arrive late, get missed, or feel poorly timed.

The Cerkl Broadcast Solution for Outlook Email Scheduling

While Outlook’s built-in scheduling tools can handle basic, one-off messages, they fall short for communicators who need consistency, automation, and insights. That’s where Cerkl Broadcast fills the gap. By integrating with Outlook and enhancing its functionality, Broadcast turns scheduling from a manual chore into a streamlined, data-driven process.

Email Scheduling Made Simple

With Broadcast, you can schedule Email Blasts in advance without relying on your device staying open or connected. Whether it’s a one-time announcement or part of a larger campaign, your message is queued in the cloud and delivered exactly when you want it to be.

Recurring Campaigns

Outlook doesn’t allow recurring sends, but Broadcast makes them effortless. Weekly newsletters, monthly reminders, or multi-phase campaigns can be set up once and automated, freeing communicators from repetitive scheduling tasks and reducing the risk of missed sends.

Optimal Send Times

Timing is critical for engagement, but Outlook offers no guidance. Broadcast uses data and AI insights to recommend optimal send times, delivering messages when employees are most likely to open, read, and respond. This feature directly addresses the overload problem highlighted by Microsoft’s 2025 Work Trend Index.

Analytics You Can Act On

Broadcast goes beyond delivery by providing detailed metrics on open rates, clicks, acknowledgments, and campaign-level impact. With these insights, communicators can refine their strategy, prove ROI, and demonstrate the value of timely, well-targeted communication.

Cerkl Broadcast Email Scheduling vs Outlook Email Scheduling

When it comes to scheduling, Outlook provides only the basics, while Broadcast delivers a purpose-built solution for communicators. The table below highlights the key differences, showing how Broadcast addresses Outlook’s limitations with a more flexible, reliable, and data-driven approach.

What’s Next

Are you measuring the impact of your emails? Too many communicators send messages without knowing if they truly connect. Our free Internal Comms Metrics Guide helps you change that by outlining the key metrics that matter most, from engagement rates to campaign performance. You’ll also see real-world examples of how organizations track and improve their internal communications.

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