How to Send Automatic Emails in Gmail (and Other Platforms) in 2025

One might assume that emails have become outdated with the growing popularity of social media DMs, Slack pings, and messenger apps. In reality, however, email remains the number one global business communication method.

That said, the email game has changed in recent years, with over 70% of consumers now expecting personalized interactions from brands — that is, emails tailored to their individual needs and arriving at the ideal moment.

Nowadays,  if you can’t deliver that level of tailored communication, your emails will likely be ignored or deleted right away, and with good reason. 

So how can companies guarantee these sky-high expectations at scale? The answer is simple — email automation. 

Businesses can now leverage advanced technology like AI-powered outreach tools to handle these time-consuming tasks, such as writing personalized messages and remembering to send follow-ups.

With the right software, all of this happens quietly in the background, enabling teams to focus their efforts on the more strategic, relationship-building activities that require an authentic human touch. 

What is email automation?

Let’s start with the basics. 

In simple terms, email automation is the practice of using software to write and schedule email messages at scale, without the user ever having to click “send”. But it goes far beyond that. 

Modern tools make it incredibly easy to set up event-based triggers to ensure emails are sent out at the most optimal time, create tailored sequences for each unique recipient, and establish custom automation “rules” (e.g., sending a follow-up three days after no response). 

Very recently, all these processes have become much smarter and more impressive thanks to AI. Now, the leading software solutions like sales email assistants will unleash AI to research each unique recipient’s data, leverage that data to craft hyper-personalized messages, and in some instances, even handle custom follow-ups and responses on your behalf. 

The two most powerful software types for email automation are:

• AI-powered outreach platforms like Reply.io that help businesses identify targeted leads, create tailored multichannel outreach sequences, and handle the entire email infrastructure, including email deliverability and analytics. 
• AI sales agents, also known as AI SDRs, that integrate into your business as fully-fledged team members, taking over the entire prospecting and outreach process. For instance, Jason AI will learn everything there is to know about your business and target audience, and then craft personalized emails (and responses) to your recipients on autopilot.   

The truth is that it’s crucial to leverage factual and relevant prospect and company data to craft truly meaningful emails, which takes a significant amount of time. Thankfully, these kinds of tools do that entire research for you. 

Outreach has also evolved into a multi-channel game. While email remains king, it has proven that outreach is much more successful when emails are integrated in a broader multichannel outreach strategy along with LinkedIn, messengers, phone calls, SMS, etc., depending on your audience. 

You could have a friendly follow-up email three days after the initial email, a LinkedIn connection request and message on day five. Though meticulously planned, every step would be completely automated, with absolutely no need for human oversight.

Benefits of automated emails 

While we’ve touched upon the importance of automating emails (and chances are, if you’re reading this, you have your own reasons), you may be wondering if it’s worth all the trouble and investment. 

Whether you’re looking for a standalone outreach platform or an AI mail drafter, the answer is an unequivocal “yes”, and here’s why: 

Save hours without cutting corners

Writing and responding to emails manually takes a lot of time and effort. By automating emails, you can concentrate on strategic work by having software handle repetitive tasks like proposal drafts, re-engagement messages, and so on. As a result, salespeople reach more prospects, recruiters reach more talents, and so on. The best part? Even when you’re not working, these tools continue to function around the clock.

Never drop the ball on follow-ups

The majority of deals are lost due to failed or forgotten follow-ups. With software, every recipient receives a precisely timed sequence with automated check-ins and reminders, ensuring that no opportunity falls between the cracks. This way, you maintain your professionalism and perseverance without the countless hours of deciding how to follow up and when. 

Personalization — at scale

Email automation isn’t about sending the same message to everyone. Modern tools can source personal information, like the name, role, or even recent online activity, and then customize each message by leveraging that information. 

With AI tools like Reply.io, you can go even further and leverage LinkedIn activity, industry news, or past interactions to make each email feel truly personal, even if it’s designed for thousands of people.

Perfect timing, every time

Automation optimizes timing, whether that means launching emails at exactly 8:30 AM in each recipient’s time zone, or having them sent based on actions that happen in real-time (like filling out a form or clicking on a link). 

The timing of your email has as much of an impact on open and reply rates as the message itself, and automation tools know exactly when to send each email and follow-up to each unique lead. 

Smarter insights, better results

Automated platforms come with tracking tools that let you see things like open rates, clicks, replies, bounce rates, and more. This lets you see what’s working and what isn’t to make the necessary changes to your outreach strategy. 

You’ll be able to tell which subject lines get more opens, which messages get more replies, and which leads are most interested. Over time, this makes your email efforts much sharper and more effective.

Scale without hiring more people

Whether you’re emailing 100 people or 10,000, automation handles the load. Startups and smaller teams can significantly scale their email outreach, without having to hire more people, which actually leads to lower operational costs. 

Flawless consistency

When you test and launch a campaign, it works exactly as you planned, with no typos, broken links, or missed follow-ups. Every person who gets your message gets it at the right time, and your brand looks professional and trustworthy at all times.

A better experience for your audience

Automation speeds up and makes communication more useful. New sign-ups get welcome emails right away, trial users get timely nudges, and customers get reminders before their subscription ends. These little things help build trust, and they happen on their own, even when your team is busy with more important things.

How to automate email outreach with Reply.io 

We’ve covered the theory, now let’s take a closer look at how email automation looks in practice. We’ll use our very own Reply.io, one of the top AI-powered outreach platforms in the market, to demonstrate this.

Initially designed as an email outreach tool, Reply has transformed over the years into a true all-in-one outreach suite that offers AI-driven personalization, a native lead database for generating leads, premium email set-up and deliverability infrastructure, analytics, and multichannel outreach, including LinkedIn. 

While it may seem overwhelming at first, the truth is, it’s incredibly easy to launch your first email outreach campaign with Reply, and once launched, you will have an AI engine generating leads and launching personalized emails on autopilot, without you lifting a finger.

Let’s get to it…

Step 1: Connect your email account

First things first, you’ll need to connect your professional email account that you’ll use for outreach to Reply.io, which is extremely straightforward. 

After signing up to the platform and logging in (shouldn’t take you more than a minute or two), head right away to Settings > Email Accounts and simply enter your email address. 

For Gmail or Outlook, it’s as simple as signing in through OAuth (click “Connect Gmail” or “Connect Office 365”) and granting permission, essentially allowing Reply to send, organize, and receive emails on your behalf. 

The great news is that once you have an account, you can connect multiple inboxes if you have multiple team members or multiple business addresses (for instance, one for sales, one for marketing, one for customer support, and so on). 

Once connected, you are officially ready for outreach and ready for step two. 

Pro tip: If you’re using a brand-new email address or domain to send large volumes, we highly recommend warming it up first to avoid getting blacklisted. With Reply.io, users will automatically warm up their domains and set up their email infrastructure to avoid spam triggers and adhere to all sending policies. 

Step 2: Import or build your contact list

Next, you’ll need to create your first list of people you plan on reaching out to, whether it’s leads, prospects, potential partners, etc. 

With Reply, you have two options. First, you can simply import your existing contact lists via a CSV file, CRM integration, or by simply entering them manually one by one. 

On the other hand, Reply also offers a native lead database with over 1 billion live contacts, enabling you to either build contact lists from scratch or significantly expand existing ones. You can simply filter your search by custom criteria like industry, title, company size, etc., and with a click of a button add the matching people to your list. 

For example, you could filter the database by “VP of Sales, in tech companies, with 50-200 employees, in the USA”, and you will instantly get a list of targeted contacts, along with verified emails, phone numbers, and other valuable data. 

Taking it a step even further, Reply.io offers an Evergreen Sequences mode that will automatically top up your outreach sequences with new contacts that match your criteria, ensuring you always have enough people to reach out to.

Step 3: Create a new sequence 

Now you’re ready for the core part of the email automation process — setting up your first outreach sequence with Reply.

Simply navigate to the Sequences tab and click “Create Sequence.” Right away, you’ll be asked to choose the type of sequence you’d like: email or multichannel. You could start off with a simple email-only sequence, as you can always add other channels and touchpoints down the line. 

Give your new sequence a name, for instance “August Promo Offer” or “Potential Partners”, and now it’s time to define the steps, in other words, what kind of messages you’d like for each step and how to space them. 

By default, you’ll see Step 1 as the initial email. Here you can write your first email template, either from scratch or letting AI create one for you (simply click the magical AI button and it will create a tailored, top-performing template). 

For example, it could look something like this:

As you can see, there are quite a few variables here, and this is where Reply’s AI shines — it will skim through your CRM (if integrated), LinkedIn, company websites, and other external sources to find all the relevant information to fill the gaps. This will be done on autopilot for each unique recipient, at scale, without you lifting a finger or spending even a minute on manual research. 

For instance, it will skim through the recipient’s LinkedIn to find the most relevant recent company update or personal achievement and use that as a highly personalized one-line opener/ice-breaker. 

Next, add a Follow-up by simply clicking “Add Step” and choosing after how many days to send it, and whether you want it as another email, LinkedIn message, or more. 

With conditional sequences, users can simply customize their sequences depending on the actions of each recipient, such as “Email follow-up after 3 days if No Reply” or “send LinkedIn connection request if Message Opened 3+ times”, and so on. 

As with the initial email, Reply’s AI engine can take care of the follow-up template and message, LinkedIn message, and even create the entire sequence on your behalf by analyzing each recipient’s profile, behavior, and preferences.

Step 4: Preview and test

Before launching your sequence, always preview and test it first. Reply.io allows you to preview each email as if it were sent to the recipient to ensure all the AI variables work correctly. You can even send a test email to yourself. 

Also, take this time to double-check the smaller details like formatting, your email signature, and that all links or attachments are functional. Ensure the sequence logic is sound (double-check the wait times, conditions, etc.). 

Finally, verify that your unsubscribe link (or compliance footer) is in place if you’re emailing cold contacts — this is required by law in most cases, though rest assured that Reply can automatically include an unsubscribe/manage preferences link within each sent email and follow-up. 

Once you’re confident that everything looks good, you’re ready for launch.

Step 5: Launch the sequence

Now that you’re set and ready, simply press the “Start” button, sit back, and let AI take care of the rest. 

Once it’s running, the system will begin to auto send emails according to your schedule, researching relevant information for each recipient to tailor each and every message and follow-up. 

You will have a dedicated dashboard showcasing what’s been sent, what’s queued, and how well your outreach is performing in real time. Keep an eye on the open and reply rates and leverage that real-time feedback to tweak your email outreach strategy on the go. 

Reply.io will monitor the progress of each sequence, so when a recipient opens or replies to your email, the platform will automatically flag it and halt further emails/follow-ups, instead pinging the user to craft a new message based on that response. 

Same goes for any unsubscribe requests or email bounces, Reply will auto-handle those contacts by marking them as “do not contact” and moving them out of your sequences to avoid harming your email domain and business reputation.

Step 6: Manage replies and scale conversations

Once the emails start going out, hopefully the responses will start rolling in. 

All incoming replies will arrive in your connected inbox (Gmail/Outlook) as usual, but they will also show up in Reply’s unified inbox, enabling you to manage incoming emails at scale, even when working with multiple mailboxes. 

In fact, many users exclusively use Reply’s interface to handle responses, as they can seamlessly tag, filter, or assign conversations with other team members. 

Remember, the goal of email automation is to spark real conversations that you or your team will then handle with a personal touch. But even here, Reply.io can help. 

With its native AI sales agent, Jason AI, users can delegate the back-and-forth email conversations to AI. Once trained on your product, business, and customer profiles, Jason AI will seamlessly take care of incoming responses by answering questions, handling objections, and even booking meetings on your behalf. 

This way, Reply will entirely take care of finding the most relevant contacts, generating tailored sequences, personalizing each email, and nurturing leads. As a result, you will simply receive a steady pipeline of warm, interested leads, and this is where a true, authentic human touch will do wonders. 

By following these steps, you’ll have an efficient, AI-powered email automation engine working around the clock in no time. You can rest assured that each email and follow-up sent will be 100% personalized with relevant information and look manually written, while your email deliverability keeps your inboxes safe and healthy. 

Each new contact that you add to Reply (or your integrated CRM) will be placed in one of your existing outreach sequences, so you won’t have to worry at all about figuring out the right timing or messaging — AI will take care of that for you. You will only need to jump in when someone replies showing interest, which will dramatically scale your conversion rates in the long run.

How to auto send emails to a folder in Outlook

Gmail is usually the most popular email platform used across the world, especially in business environments that send tons of emails to “outsiders”. However, there are also numerous companies that use Outlook for their internal and external communications due to its seamless integration with the Office suite. 

As a result, most modern outreach tools come with built-in support for connecting to both Gmail and Outlook. 

That being said, email automation isn’t just about cold outbound outreach. Managing the flood of emails that come into your inbox every day, including newsletters, alerts, inbound leads, etc., is also a part of it. 

This is where Outlook really shines.

The “Rules” feature in Outlook lets you automatically sort incoming emails to custom folders based on the sender, subject line, or keywords, keeping your inbox organized and focused in the long run. 

Here’s how to auto send emails in Outlook using Rules:

• Make your folder → To make a new folder, right-click on your Inbox (or another folder) and choose New Folder. Give it a name that makes sense, like “Reports,” “Newsletters,” or “Inbound Leads.”

• Open the Rules menu → Simply go to Home > Rules > Manage Rules & Alerts > New Rule.

• Set your condition(s) → Choose what will set off the rule: the sender, the subject line, or custom keywords. If needed, you can combine more than one condition.

• Choose your action → Choose “Move item to folder” and then pick the folder you made earlier as the destination.

• (Optional) Add exceptions → You can make the rule more specific by leaving out important senders or certain situations. Skip this step for basic filtering.

• Complete and test → Save the rule. You can also apply it to messages that are already in your inbox. Send yourself a test email next to make sure everything is working.

And there you have it, pretty simple. Once these rules are set, Outlook will automatically sort all incoming emails in the background, even when you’re signed out and have your devices closed. 

For those wondering how to auto send emails to a folder in Gmail, here’s the brief official guide — it’s pretty straightforward, just slightly less customizable than Outlook. 

It goes without saying that you’ll still need to connect it to a proper outreach tool like Reply.io if you want to automate your outbound emails. 

The strategic value of email automation in 2025

We’ve talked about a lot of things, like why email remains the most popular business communication channel and how to automate email outreach at scale without sacrificing quality.

The main takeaway — email automation doesn’t just save you time, it gives you and your business a competitive edge.

Whether you’re running sales sequences, marketing drips, recruiting flows, or just organizing your inbox, automation helps you move faster, stay consistent, and create more opportunities. It’s the difference between touching base with 20 or 200 leads a day, without missing a beat.

Start small, check out Reply.io and launch your first automated, AI-powered email sequence, and take it from there.