Perhaps you want to tidy up your inbox and remove some of the conversations you no longer need from the sent folder. If this is the case, you will be happy to know the answer is “yes”—you can delete sent emails in no more than a few clicks.

Now, things get slightly more complicated if your goal is to revoke a sent email and remove it from the recipient’s inbox. 

In this guide, you will learn whether deleting an email you sent is possible

 and what features of different email providers you can use to achieve that.

Access Skiff Mail’s advanced encryption for secure emailing and get nifty features like undo send 

Regain control over your communication

If you want to delete an email from the sent folder, you can do so quickly with virtually all 

 as examples. Both platforms feature a similar layout, so you can take these steps in both:

Navigate to the email you wish to delete and hover over it with your mouse

Click the bin icon on the right side of the email

In Gmail, your deleted emails will be moved to 

, so you have ample time to undo this action if you believe you might still need the deleted email in the future.

If you want to remove sent emails for good, you can navigate to the dedicated trash folders and do it from there. Gmail makes it easier because you can click the

 button and delete all emails from the folder in one click.

Outlook doesn’t have such a button. Instead, you’ll see the one that lets you 

 in a single click, but the mass deletion option is slightly less apparent. 

 on the left side of the ribbon menu to empty the folder.

If you’re struggling with receiving unsolicited emails, you can check out these guides on 

When you delete a sent email, the action only removes it from the corresponding folder in your email app. 

The deletion doesn’t impact the recipient’s inbox

Still, there may be a workaround for this

if you use Gmail or Outlook, as both apps offer features geared toward damage control in case you accidentally send an email.

After you send an email in Gmail, you get a short time window to delete/unsend it. You only get five seconds by default, but 

you can extend the window by taking these steps

Click the gear icon in the upper-right corner of the screen

You’ll now have more time to recall an email you sent accidentally. The undo option will 

appear automatically in the bottom-left corner

 of the screen as soon as you send the email. When it does, click 

, where you’re more likely to make a mistake while emailing on the go. The 

 button will appear at the bottom of the screen, and you won’t miss it.

Unlike most email services, Outlook lets you fully recall a sent email or replace it with the correct version. It doesn’t have a predetermined time window like Gmail’s equivalent option, but 

you can only recall the message until the recipient has opened it

You can take the following steps to access this option:

Find the email you wish to recall and open it (make sure to double-click the email as a single click only shows it in the reading pane without actually opening it)

You’ll see a pop-up window asking whether you want to delete unread copies of the message or replace them with a new version. Choose the appropriate option and click 

you’ll get a report showing whether the recall was successful

, but you can uncheck this option in the pop-up window if you don’t need it.

As useful as this option may be, it comes with a 

You cannot recall a message in Outlook on the web—the option is 

Recalling an email is only possible if the recipient has a Microsoft 365/Exchange account 

If Azure Information Protection applies to a message, 

The dangers of sending sensitive information via email

 is not as easily fixable as attaching a wrong file or CC-ing a wrong person. Once your data reaches the recipient, you might lose control over how it is used or distributed further.

Worse yet, using a typical Big Tech platform (Google, Outlook, Yahoo, etc.) exposes you to the 

 before it even reaches the recipient. This exposure mainly happens for two reasons:

 encryption protocol to protect data in transit. 

intercepted through a man-in-the-middle attack

 can get a hold of your information somewhat effortlessly.

Encryption key ownership further exacerbates this issue. Encryption keys used to encrypt and decrypt your emails are 

created by the email provider and stored on 

, which means they can decipher your emails and read plaintext copies. Your data isn’t as private as providers want you to think, so you should 

be careful about the information you share

The good news is—you can mitigate these risks by steering clear of Big Tech services and 

Benefits of using a privacy-first email service

 let you share personal information more confidently, as the risk of it falling into the wrong hands becomes minimal. Several important security measures make this possible, most notably 

E2EE assures your security and privacy in several ways, and the table below highlights the most important benefits of its mechanisms:

 of services like Gmail or Outlook, the main protection layer you’ll get is S/MIME. Besides 

, this protocol requires a complex setup and a 

certificate you must buy separately and configure in your email service

—a time-consuming process that may be too technical for an average user.

Luckily, a handful of privacy-first email providers ensure you get advanced security without extreme efforts or investments. If that sounds appealing, 

Skiff Mail’s military-strong encryption is accessible to each user

Get instant data protection

Regain control of your data with Skiff Mail

 as the top priority. It safeguards each email you send using two separate keys—public and private.

 and is shared with the recipient. The private key is mathematically related to the public key and used to decipher the email, and it 

remains safely stored on the user’s device

, so even their team can’t decipher your correspondence—everything you share stays between you and the recipient.

Strong encryption isn’t the only way Skiff Mail 

, you’ll access a beautifully designed, user-friendly interface that makes the platform easy to use for beginners and advanced users. Despite its simplicity, Skiff Mail boasts numerous useful features, such as:

—You can leave yourself more time to double-check an email by scheduling it or recall a message if you’ve overlooked something

—Unlike many E2EE email services, Skiff Mail provides lightning-fast search that lets you browse emails’ contents for specific information

—Skiff Mail offers 10 GB of end-to-end 

, which is far above the industry standard (typically 1 GB with popular services)

—You can use Skiff.com aliases to manage emails from multiple addresses in one inbox and organize them with labels, folders, and filters

—Skiff Mail lets you personalize your email address and signatures to express yourself or sound more professional

. No important feature hides behind a paywall, and the free plan doesn’t expire.

Your Skiff account doesn’t only give you access to a 

 three additional end-to-end encrypted tools 

to help you create a safe, streamlined workflow:

—Lets you create elaborate notes and documents thanks to a rich text editor and support for all content types. You can collaborate with your team in real-time, and your files’ contents and key metadata will be end-to-end encrypted

—Supports files of all types, storing them securely in an E2EE 

. You can choose to integrate Skiff Drive with the InterPlanetary File System (IPFS)—the largest decentralized file storage solution on the web

—Helps you stay organized and automatically syncs with Skiff Mail. The platform also comes with a built-in video conferencing tool, so you can host private meetings and events

, and Windows (through a browser). Visit the 

If you want to safeguard your correspondence, you can sign up for Skiff Mail by taking the following steps:

If you’re hesitant to switch from your current email service out of fear you’ll lose important correspondence, Skiff Mail has a solution. Thanks to 

Can you delete an email you sent? Answered

—you never know when you’ll need a seemingly trivial work email from two years ago.

While some email service providers and third-party tools can automate 

, you can only trust these processes up to a point. Even with the most meticulous filters, a vital email might get deleted without your knowledge.

Does Gmail delete old emails when your storage is almost full? This article will answer the question in depth and help you find the best solution for managing your inbox without deleting crucial messages.

Skiff Mail is a security-fist solution with numerous inbox management features for clean emailing

Keep your inbox in check

Does Gmail automatically delete old emails?

Gmail doesn’t automatically delete any emails

You can have an email from a decade ago on Gmail, and the platform won’t delete it—even if your 

. Once you reach your storage limit on Gmail, you won’t be able to receive any new emails, but old messages remain intact.

The only time Gmail automatically deletes an email is when it’s been labeled as Trash for 30 days.

 Gmail manages emails with a system of labels applied to each message. Inbox is a label, and so is Trash. You can access these labels from the left-hand menu in Gmail.

When you delete an email, Gmail removes the Inbox label and applies the Trash label to the message

, effectively removing it from your Inbox and moving it to the Trash menu.

By default, emails stay in the Trash folder for 30 days.

 from there, but after the 30-day period, the provider will permanently remove the message from your account.

Bear in mind that this doesn’t mean Google hasn’t kept your emails somewhere on their servers or in offline storage it uses for backups. The same is true for most providers that may retain access to your emails long after removing them from your account and they become unavailable to you.

How to delete all emails older than a certain date in Gmail

To remove all messages past a specific date in Gmail, you have two options:

How to delete older emails in Gmail from the search bar

the Gmail search bar can be a powerful tool for finding specific messages or a range of emails.

you’ll need to learn the basics of Gmail search operators

. These are parameters you can use to refine your searches and filter emails by criteria like:

The “before” operator helps find and delete older emails.

 If you wanted to see all emails received before August 1st, 2023, for example, you’d type 

 in the search bar. The date format is year-month-day.

To delete all emails past a specific date, follow these steps:

 by clicking the checkbox above the search results

. This action will effectively mass-delete everything from that period.

How to delete older emails in Gmail by creating a filter

While useful, search operators are a manual, one-time solution for deleting older emails. 

they can automatically categorize emails according to predefined criteria, including age.

You can set up a filter that applies a certain label (like Trash) to all emails older than a specific date or period. After that, you’ll be able to choose what happens to any matching emails, which is when you’ll opt for deletion.

To create a filter that deletes older emails, follow these steps:

‘Select what to do with matching conversations’ 

operator is versatile—you can use it to set any number of years, months, or days. For example, to automatically delete all emails older than two years, you’d enter 

examples of how you can use the older_than:X parameter 

The filter applies to all messages, including 

Since Gmail doesn’t delete emails automatically,

 the most likely cause of a missing email is you deleting it yourself

. If you’re positive you haven’t done so, the email could also be:

Check if your email was archived or marked as spam

When you archive an email in Gmail, the platform removes its Inbox label, but the message is still accessible through All Mail.

suspect the email has been marked as Spam or moved to Trash

Enter any keywords from the email you remember in the ‘Has the words’ prompt

This might also be a good time to manage your Spam folder and avoid future junk mail from filling up your storage. Check out these guides on 

permanently stopping spam emails on Gmail

Check if you’ve forwarded the message to another account

If you’re forwarding emails from Gmail to another account, you may have accidentally deleted the original messages in the process. 

Gmail’s forwarding settings let you choose between:

Follow these steps to check your current forwarding settings:

 it’s probably why your emails are missing.

Check if an email filter is deleting your emails

If you’ve set up a filter to delete emails past a certain date or older than a specific period, 

the filter is probably to blame for your missing messages

To check whether you’ve created such a filter, follow these steps:

Select the checkbox next to any filters that include the following actions:

Any messages that the filters deleted over 30 days ago will not be accessible

, as Gmail has already permanently removed them from Trash. Otherwise, you’ll be able to 

 from Trash or All Mail, depending on the filter.

Check if emails are inaccessible due to email client issues

You can access your Gmail inbox using different email clients, such as Apple Mail or Microsoft Outlook. In that case, the client downloads emails from Google’s servers via POP or IMAP protocols.

Your POP and IMAP settings in Gmail may be to blame for your deleted messages. Similarly to forwarding, 

you might have enabled deleting emails from Google’s servers after sending them to the client.

Follow the steps below to check your POP and IMAP settings:

Does Gmail delete old emails? What you should know

While organizing your emails, you might accidentally delete a message containing information you’ll still need in the future. Luckily, you should be able to recover such emails in most cases, especially if you’ve deleted them recently.

how to retrieve a deleted email with major 

, including Gmail, Outlook, and Yahoo, even if they’re removed from your inbox permanently. You will then learn about important 

 and privacy concerns regarding deleted emails—something to consider if keeping data safe is your priority.

Skiff Mail is a privacy- and security-first service that lets you stay in control of your inbox

Manage your email securely

In Gmail, deleted emails go to the Trash folder, and you can 

 from there within 30 days. Here’s how:

Navigate to the folder list on the left side of your inbox

If you want to recover emails to a specific folder, you can do that from the drop-down menu instead of the main inbox. You can also 

 if you’re sure you won’t need them anymore or if they’re 

Alternatively, you may need to reference an email removed from Trash either automatically or directly by you. In any case, 

you can only recover such emails through the Google Admin console

If this applies to you, restoring permanently deleted emails is possible for 

. You (or someone with the administrator account) can sign into the Admin console and choose the 

After 25 days, your only chance of recovering deleted emails is if your organization uses Google Vault and the emails are 

. This is a highly specific scenario, so this method might not apply to most emails.

If you accidentally delete an email, Gmail will give you a small time window to undo this action. An Undo button will appear in the bottom-left corner of the screen, and you can click it to restore the email immediately.

. After this, you can go to the Trash folder and recover the email from there, as explained above.

 is similar to that in Gmail. Here are the steps you should take:

 folder in the left-hand menu of your inbox

Click the folder icon in the ribbon menu above the inbox and choose the folder you want to move emails to

Much like in Gmail, you can also undo the email deletion, but 

Move the slider to choose your preferred time frame (up to 10 seconds)

How to recover deleted emails from Outlook after 30 days

Outlook holds onto deleted mail for 30 days, after which they’ll disappear from your account permanently. Still, you may be able to 

 (note that this option is only visible if you have any retrievable emails)

Right-click the email you want to recover and click 

 restore the retrieved email to its original folder

. If it was a custom folder you deleted in the meantime, the email will go to your main inbox instead.

Note that this feature might not always yield the desired results or bring back all your deleted emails, in which case Microsoft recommends the Email Recovery plugin. Still, many users have 

For more detailed instructions on managing your Outlook account, you can read these guides on 

Yahoo’s email recovery option looks slightly different but is still straightforward. You can restore deleted emails by taking these steps:

you can’t choose the folder you’ll move an email to

. You can still sort the email as usual once it’s back in your inbox. Another disadvantage is a 

More importantly, all emails from trash are deleted automatically after seven days, so you have much less time to recover them. When this timeframe ends, 

, which you can do for seven additional days before your emails disappear permanently.

 button in the upper-right corner of your inbox to enter Yahoo’s main screen

Click on your profile icon (again in the upper-right corner) and choose 

Under Email, click Recover lost or deleted emails

You can also use this method to recover missing emails from folders like Sent or Archive.

Tread lightly with third-party email recovery apps

Every major email service offers recovery options for deleted emails. If they don’t work, you may be tempted to use a third-party tool. Doing this may not be wise because the cost might outweigh the potential benefit.

In this case, “cost” doesn’t only mean the actual app purchase but something far more valuable—

Email recovery apps need access to your correspondence, and they 

may not implement adequate security measures

 to safeguard your login credentials and other sensitive data. In fact, the same goes for your email provider, particularly if you have an account with a Big Tech service like those discussed here.