Microsoft Outlook has so many bugs it might as well be called a jungle. This article will cover how to fix Outlook issues that plague every user in 2021.
Regardless of which email client you have chosen, Mailbird wants to get to the bottom of the many issues with Outlook.
Whether it’s Outlook password prompt issues or the authenticator app not working, we know that users are frustrated with the software. Not to mention, try explaining what happened to Hotmail, MSN, and Windows Live email accounts.
We’ll cover syncing up devices and troubleshoot why Outlook sometimes says it’s not responding, how to avoid PST file corruption, and how to manage your junk mail folder.
Also, if you’re considering throwing in the towel, we recommend switching from Outlook to another email client. We’ll tell you a bit about what Mailbird can do for you.
Email Account Access
Outlook is the official name of Microsoft’s email service. It’s available two ways: via web browser at outlook.live.com and as an email client you access like you would an application on desktop or mobile.
You can link up to 20 different email accounts to the 2019 version of Outlook. That means, in addition to an @outlook.com email address, you could also direct your emails from your @gmail.com address to your Outlook inbox.
Setting up email with Outlook is tedious. Users feel the platform is not designed intuitively, and there have been a lot of changes to keep up with.
You see, Microsoft has also had email services under the following names: Hotmail, Windows Live, and MSN.
Some of these accounts still exist as legacies, but it’s confusing to sort through what is being phased out and what will remain available.
We have created some tables to clarify how to access your email account using Outlook if you are still signed up for one of the providers Microsoft used to champion.
Hotmail
Hotmail.com in 2021
Hotmail.com now redirects you to Outlook.live.com.
You can still create a new email address with @hotmail.com as the domain name.
Existing Hotmail accounts have been permitted to keep their email addresses as well.
How to Access Hotmail Via Web Browser
Hotmail now uses Outlook.com’s email sign-up as its dedicated web browser sign-in page.
- Go to https://outlook.live.com/
- Use your Hotmail account email address to fill in the email field.
- Use your Hotmail password to fill in the password field.
How to Recover an @hotmail.com Account
If you have not logged in to your email address in over two years, it will be considered inactive and may have been removed.
If your Hotmail account has been active in the last two years, there are two ways to regain entry:
If you do have two-factor authentication enabled on your Hotmail account, you can go to the Outlook login page and follow the steps to recover your password by offering verification through your phone number or back-up email.
- When prompted for your password, click “Forgot password?”
- Select where you would like a verification code sent to. If it’s a secondary email, type out the email address without the asterisks (to complete the hidden part”).
- If you’re verifying with a text message, you’ll have to complete the hidden part of the phone number.
- Microsoft will then send out a code for you to enter. After that, you can begin the steps to reset your password.
If you do not have two-factor authentication enabled, you can fill out the account recovery form.
Most importantly, you will be asked to provide details like your full name and date of birth, when you created the account or last used it, or contact list details to prove the account is yours.
Upon a successful review, Microsoft will email you with steps to reset your password and recover your account.
How to Add a Hotmail Inbox to Outlook
There are two ways to add your email address to Outlook 2019.
Auto Account Set Up:
- Open Outlook.
- Select File and click on Add Account.
- Enter your email address and select Connect.
- Enter your password.
Manual Account Set Up:
- Open Outlook.
- Select File and click on Add Account.
- Enter your email address and select Advanced Options.
- Click on “Let me set up my account manually” and then select Connect.
- Select between IMAP or POP3. Note: Outlook uses IMAP by default. Then click Next.
- Check that the settings match the information in the image below:
- Provide your password and select Connect.
How to Access Hotmail on an iPhone
- On your iPhone open Settings.
- Select Mail.
- Tap Add Account.
- Select Outlook.com.
- Under “Let this app access your info?” click Yes.
- Enter your Hotmail account details.
- Scroll to Mail Days to Sync and select “No Limit.”
- You may be sent an email asking you to confirm you allowed the sync. Go to your web browser to confirm this email.
- Open your Mail app to see if your emails have synced.
MSN
MSN.com in 2021
MSN.com is still an active webpage. The page serves as a homepage for many people because it includes a link to Outlook, a weather update, aggregated news tailored to you, and Bing (Microsoft’s search engine).
You cannot create a new email with @msn.com as the domain address.
If you have an existing MSN email you can still log into it with Outlook.
How to Access an MSN.com Email Account via Web Browser
Go to https://outlook.live.com/.
Use your MSN email address to fill in the email field.
Use your MSN email password to fill in the password field.
How to Recover an MSN Email Account
If you have not logged in to your email address in over two years, it will be considered inactive and may have been removed.
If you have logged in within the past two years but don’t remember your password, you can try the Microsoft Recovery Page (see the Hotmail table above for more details).
How to Migrate MSN Email to Outlook.com Email
- Open Outlook and select File.
- Go to Account Settings.
- Select Email and click New.
- Choose Server Settings.
- Under User Data enter your name and your MSN email address.
- Choose IMAP.
- Fill in the following details:
Incoming e-mail: imap-mail.outlook.com
Incoming port: 993
Outgoing email: smtp-mail.outlook.com
Outgoing port: 587
- Add your MSN email details under Login Settings.
- Ensure that Login with Security reads: SSL.
- Select Test Account Settings.
How to Access MSN on an iPhone
In the same vein, MSN is connected to Outlook, you can add your MSN email to your iPhone the same way you would an Outlook or Hotmail account (see Hotmail section for screenshots).
- On your iPhone open Settings.
- Select Mail.
- Tap Add Account.
- Select Outlook.com.
- Under “Let this app access your info?” click Yes.
- Enter your MSN account details.
- Scroll to Mail Days to Sync and select “No Limit.”
- You may be sent an email asking you to confirm you allowed the sync. Go to your web browser to confirm this email.
- Open your Mail app to see if your emails have synced.
Windows Live
Live.com in 2021
Live.com now redirects to outlook.live.com.
You cannot create a new email address with @live.com as the domain address.
You can still log in to Outlook with a legacy @live.com email address.
How to Access Windows Live on a Web Browser
Go to https://outlook.live.com/.
Use your Live account email address to fill in the email field.
Use your Live password to fill in the password field.
How to Recover an @Live.com Account
Live.com addresses are gone forever when they are deleted.
If your account hasn’t been active in over 270 days, it is considered inactive. After 365 days it will be deleted.
If you have logged in to your @live.com email address in the last 12 months but don’t remember the password, you can try the Microsoft Recovery Form.
How to Migrate Windows Live Email to Outlook.com Email
For users who have the discontinued free email client Windows Live Email, you’re likely finding it’s high time to export your email to Outlook.
- Close Outlook.
- Open Windows Live Email.
- Click on File and go to Export Mail.
- Select Email Messages.
- Select Microsoft Exchange and click Next.
- In the Profile Name Menu, select Outlook.
- The Export Messages dialogue box will ask you to select All Folders or Selected Folders. You can select either option, depending on what you need to export.
- Once the export progress box shows the status as complete, go to Outlook to check for your files.
Outlook Sync Issues
Through the myriad of questions we have seen on Quora, Microsoft forums, and Reddit, we have learned that Outlook’s number-one issue for many is a little message that says “Problem connecting to server.” Here is how to fix outlook issues relating to connectivity and syncing your email.
To troubleshoot the “Problem connecting to server” message, you can do the following:
- Open Outlook and select File.
- Go to the Account Settings.
- Select Repair Account.
- A Repair Account window will prompt you for your email address and password. Then it will run a program to diagnose the network connection problem.
If the repair account process is not sufficient, you can certainly try to pinpoint the issue by looking at the following strategies.
Outlook Not Receiving Emails
Full Inbox: You may have to delete some emails to make room for new ones to arrive.
Junk Folder: Some emails might be landing there because they have characteristics of spam.
Too Many Accounts: You must have 20 or fewer accounts synced to Outlook.
Review email sorting settings: You may have a filter hiding recent messages. To fix this:
- Go to your Outlook inbox and select Filter.
- Sort by Date to ensure you’re reading the latest incoming emails.
Check blocked senders and safe senders lists: Your inbox may have blocked emails from someone who should actually be a safe sender.
- In Outlook, go to Settings.
- Select Mail and go to Junk email.
- Check the Blocked Senders list for any addresses you would like to move to the Safe Senders list and vice versa.
Check Rules: Outlook lets you set up different rules for different emails you receive. You can check to see if you’ve assigned a specific action to emails in your inbox.
- In Outlook, go to Settings.
- Select Mail and go to Rules.
- Look at the Inbox Rules and Sweep Rules.
- Delete any rules you do not wish to enable.
Outlook Not Sending Emails
Internet Connection: In the bottom of your Outlook window it will tell you if you’re connected to your email server. If it says “Working Offline,” “Trying to connect,” or “Disconnected” you will need to resolve your network issue to send emails.
Daily Message Limits: You have exceeded how many emails you are permitted to send in a day. A verified @outlook.com email address can send 300 emails a day. Moreover, there is also a maximum of 30 emails a minute. The most recipients that can be added to one email is 100.
Junk Email Filter Triggered: There could be something in your content that triggers the junk email filter and blocks your content from arriving at its destination. Check to see if you’ve sent something with keywords like “cheap” or “casino” that could be triggering this.
Outlook Keeps Freezing / Outlook “Not Responding” Message
There is nothing worse than when you are working on something important, you go to send off an email, and Outlook freezes or you see that dreaded “not responding” message.
There are a number of causes to Outlook not working you can troubleshoot. If you want to learn how to fix Outlook issues involving a frozen screen, here are some things you can do.
Outlook (or Your Device) Is Busy with Another Project
If you’re migrating or deleting a large file, it might be occupying Outlook to the point that it cannot process another task.
How to Check on What Is Running in the Background:
- Check the status bar of your project (usually in the bottom left-hand side) and wait for it to complete.
- On your computer, you can select Alt + Tab to check for other dialogue boxes that might be blocking Outlook.
- Close anything you’re finished with and refresh Outlook.
Update Outlook
If you haven’t made it possible for Windows Updates to be automatically installed on your computer, then it might not be performing at its peak and needs to update.
How to Update Outlook:
- Open Outlook and select File.
- Choose Office Account.
- Click on the Update Options button.
- Select Update Now from the menu to check for new updates to Outlook.
Update Windows
The same idea for updating Outlook applies to your entire operating system. It’s worth running a quick check to see if there are any updates that can improve the experience with all of your software.
How to Update Windows:
- On your computer, go to the Start button, then select Settings.
- Search “Check for updates” or Choose Update & Security and select Windows Update.
Disable Add-Ins
Add-ins are a pretty frequent culprit for Outlook lagging issues because they are meant to provide additional functionality, but they put additional pressure on loading time.
How to Disable Add-ins on Outlook:
- In Outlook go to File and select Options.
- Select Add-Ins.
- Select Manage from the dropdown list and click Go.
- Click Remove for any add-ins you’d like to disable.
- Restart your Outlook.
Check Your Mailbox Size
The folders storing all of your mail might be struggling to run because of how large they are. You can set up auto archiving to smooth out some of this issue. You should also keep reading about how to fix another typical outlook issue, PST file issues.
How to Set Up Auto Archiving in Outlook:
- In Outlook select File and go to Options.
- Choose Advanced.
- Go to AutoArchive and click on AutoArchive Settings.
- Select Run AutoArchive every n days.
- Choose how often to run AutoArchive. The default is every 14 days.
You can also choose to have Outlook delete emails after they reach a certain age.
Note: If your Outlook is connected to an organization, there may be a configuration set by the system administrator restricting this change.
Check PST File Issues
It’s incredibly common to have Outlook crash because of a corrupted PST file. Scroll down for an entire section on this specific issue.
Disable Your Antivirus Software
It might be that antivirus software is trying to block a function that is repeatedly trying to squeeze through the firewall. Try disabling it and see if Outlook freezes less.
This is one of the more popular culprits as to why Outlook repeatedly asks for your password. Scroll down to read more about disabling this software.
Check Your AppData Folder
The AppData folder hosts a lot of files, including bookmarks and cached pages. It might be redirected to a network location. This might be slowing down or overriding other commands in Outlook. To disable this feature, you’ll need to edit the Windows Registry.
How to Use the Windows Registry Editor to Stop AppData Redirection:
- Exit Outlook completely. Ensure it is not running in the background. (You can do this by pressing Ctrl+Alt+Delete -> Task Manager -> Processes.)
- Press the Windows logo key + R on your keyboard to open Run.
- Type “regedit” (without quotes) and press Enter. The Registry Editor will open.
- Cut and paste this into the Registry Editor search bar: HKEY_CURRENT_USERSoftwareMicrosoftWindowsCurrentVersionExplorerUser Shell Folders.
- Hit Enter.
- Locate the value AppData. Double-click on it.
- Type %USERPROFILE%AppDataRoaming into the Value data area.
- Click OK to save the changes. Exit the Registry Editor.
Authenticator App Issue
The Authenticator app is designed to help you quickly and safely confirm your identity.
With the app, an online intruder would be stuck on the first step of verification, because the Authenticator app is awaiting a one-time passcode, your fingerprint, another password, etc.
The major complaint we see from Outlook users is that the Authenticator app won’t recognize certain devices. For example, if you switched phones, the app is awaiting authentication from your old device.
Some Microsoft Accounts Require a Special App Password
In typical Microsoft fashion, there are also additional rules for certain older platforms that will make you feel very confused about 2FA. We’d be remiss to not tell you there are certain accounts (like Xbox 360) that always require 2FA as well as a special app password.
If you’re entering a password you know is correct and getting a message that says “incorrect password,” then you’ll want to read this page.
Whether you’re determined to turn off the Authenticator app or simply get it onto your new phone, here is some advice for you.
How to Disable the Authenticator App
- Go to Microsoft’s Account Security Page. You will need to sign in.
- Select Advanced Security Options.
- Select Turn Off under Two Step Verification.
- Click Yes to confirm.
How to Set Up the Authenticator App on a New Phone
First things first, this requires thinking ahead. You’ll need to still have your old phone with you, so you can turn on the backup option there. After that, you can go through Microsoft’s Recovery Tool on your new device to gain access to your Authenticator app.
How to Turn on the Backup Option on the Authenticator App:
- Open the Microsoft Authenticator app.
- Click on the three vertical dots in the corner of the app.
- Open Settings and scroll down to Backup.
- Slide the bar to enable “Cloud Backup” or “iCloud Backup.”
Enabling this will back up your usernames and codes to the account you used to create the Authenticator app. Keep your old phone handy; you’ll need it after you have set things up on your new one.
How to Use the Microsoft Recovery Tool:
- Install the Authenticator app onto your phone, but don’t set up an account yet.
- Instead, click the Begin Recovery button.
- Sign into your accounts from your new phone to enable the tool to ask you to revalidate them.
Once you have tested all of your accounts on your new phone, you are finished with the Recovery Tool, but not with the transition:
- Open your old phone.
- Remove accounts from your Authenticator app.
- Remove the Authenticator app from your old phone.
Authenticator Only Allowing iPhone Touch ID
If the app doesn’t seem to be cooperating with your iPhone unless you use Touch ID, you can try the following:
- Open iPhone Settings.
- Scroll to Touch ID & Passcode.
- Turn off the “Use Touch ID” option for the Authenticator app.
Note: you may have to delete stored fingerprints as well.
- Restart your iPhone.
- Reopen the Authenticator app, and it should ask for a passcode instead of Touch ID.
Outlook Repeatedly Asks for Password
Outlook has a bug where it repeatedly prompts you for your password, even after you’ve logged in. This slows down productivity and quite frankly is just a total nuisance. There are standard customer service tips Microsoft provides, but more often than not, we’ve noticed this particular issue tends to force the user to seek out advice from forums and other tech support services.
There are a number of reasons this issue arises, which makes it even more infuriating. It could be an issue with a setting on the account, or it could be something external that is blocking normal functions in Outlook.
Here is a list of things to try to stop getting that pesky password prompt after every action you do on Outlook.
Password Expiry
Administrators can set up an expiration date for passwords, so if your workplace or organization has this setting enabled on your desktop, you may be trying to enter what you think is your correct password and getting denied. You should be able to go to Outlook via a web browser and reset your password.
Update Outlook
It could be as simple as an out-of-date version of Outlook’s software. Once an update has been run on your system, the bug may be rectified.
How to Update Outlook on Your Desktop Computer:
- Open Outlook and select File.
- Choose Office Account.
- Click on the Update Options button.
- Select Update Now from the menu to check for new updates to Outlook.
Check Settings for “Always Prompt for Passwords”
Check your settings to see if you’ve got the “always prompt for password” feature enabled.
How to Check Whether the “Always Prompt for Passwords” Setting Is on:
- Open Outlook and select File.
- Choose Account Settings.
- Click on your Exchange account.
- Select Change and click on the More Settings button.
- Find the Security tab.
- Look at the User Identification section and check whether “Always prompt for logon credentials” is selected.
- If it is, disable it and restart Outlook.
Disable Your Antivirus Software
If you have additional software for protecting your computer, see if it’s blocking Outlook from running properly.
The easiest way to find out if this is the problem is to temporarily disable your antivirus software and log in to Outlook as usual. If the prompts go away, you’ll know it was the antivirus software.
Every antivirus software is different, so you’ll want to look up how to specifically enable Outlook with the software you’re using.
We can say that you will likely need to reinstall your software and reconfigure the firewall settings. Often there is the option to add sites to a whitelist, and you can give more permissions to Outlook.
Credential Manager
The Credential Manager is where Windows stores passwords and login information on your computer. It acts as a vault with specific settings and permissions you can adjust.
If you are using Outlook on a PC, you can check to see what is currently permitted by your computer or try to reset the Credential Manager and remove any old passwords. This is similar to clearing the cache on your browser.
How to Remove Outlook Credentials in Credential Manager:
- Go to the Start Menu and select the Control Panel.
- Select Credential Manager.
- Find the credential sets that have Outlook in the name.
- Expand the set and click on Remove from Vault.
- Repeat the steps for all credential sets that have Outlook in the name.
Create a New Outlook Profile
The issue might be difficult to identify if you have multiple accounts and a long history with Office 365, Exchange, and Outlook. Unfortunately, the transitions from different versions have caused a lot of bugs. In this case, it might be easier to just create a new profile.
How to Create a New Outlook Profile:
- Exit Outlook.
- In the Start Menu select the Control Panel.
- Click on Mail.
- Click Show Profiles.
- Click Add.
- Enter the name of the profile (your name) and click OK.
- Enter your email and name in the fields if it doesn’t automatically fill it in by default.
- Click Next.
- Click Finish.
- Back in the Mail window, select your new profile in the “Always use this profile” dialog box and click Ok.
How to Fix a Weak Spam Filter for Outlook and Hotmail
Unfortunately, it can often be hard to decipher whether or not an email is harmful all on your own.
Many factors set off spam filters — the IP address, domain reputation, language used in the email (certain keywords like “free” and “casino,” for example), and subscriber complaints, to name a few.
Mind you, a spam filter should not be so ironclad that anything remotely unfamiliar isn’t making it to your inbox. Outlook hack articles flag this as a frequent concern for those relying on Outlook for their internal communication.
If you’re finding the Hotmail spam filter isn’t great, or you’re concerned about how secure your inbox really is, there are some solutions:
Blocked and Safe Senders Lists
Outlook has a location where you can manually add approved email addresses to the Safe Senders list and ensure they never end up in your junk mail.
- Open Outlook and click on Junk Email.
- Click Junk Email Options.
- Manually add emails to the Safe Senders list.
- Review the Blocked Senders list and remove any approved contacts.
You can also instruct Outlook not to trust anyone not on your Safe Senders list if you’re very concerned about security, but at the risk of having lots of contacts land in your junk mail folder.
Use Anti-Spam Software
If you’re particularly worried about accidentally clicking on a phishing link or your personal information being compromised, it’s a good idea to get yourself a digital bodyguard in the form of third-party software.
Anti-spam subscriptions can be installed to your desktop in addition to a plug-in for your web browser. The software will block any unwanted emails from its own comprehensive blacklist and use anti-virus technology to scan inbound emails for malware, phishing scams, and other harmful content.
Look for anti-spam software that also flags websites you visit, enabling you to scan for and prevent online viruses.
Use Gmail as Your Email Provider
Gmail has a positive reputation when it comes to spam filtering. Using them as your email provider in tandem with your email client means you can enable their anti-spam features, which are superior to Hotmail and Outlook.
PST File Issues
The PST (Personal Storage Table) is where all of your data (emails, contacts, attachments, and even configuration settings) are stored. Much to the dismay of Outlook users, the PST file seems to be really sensitive.
Files are constantly corrupted for any number of reasons. Problems with the device, connection to power, network issues, viruses or malware, oversized files, and improper shutdowns all cause the PST file to act up.
We have created a list of solutions to common PST file issues.
How to Repair a Corrupted PST File:
The good news is that Outlook has a built-in tool to scan for corrupted files.
How to Run the Inbox Repair Tool (ScanPST.exe)
- First, locate the PST file that is corrupted.
- By default, the PST file can be found on your computer here:
C:Users%username%DocumentsOutlook Files
Or
- Open Outlook and select Account Settings.
- Select Data and browse to find the location of your Outlook Data Files.
- Next, launch Scan PST.
To launch, type: C:Program FilesMicrosoft Officerootoffice16 into the search bar on your computer.
- Open the file. Search “ScanPST” in the right-hand search bar.
- Select the corrupted PST file you’d like to run repairs on.
- Click Start. This begins the scan process.
- A message will appear to show you the number of folders and items found in the PST file and how many errors have been found.
- Select “Make backup of scanned file before repairing.”
- Then click on Repair.
- Restart Outlook once it says “Repair Complete.”
The bad news is that the ScanPST.exe program doesn’t work for severely corrupted files. You’ll need to acquire a recovery tool designed for bigger jobs. Search “PST Repair Tool” and you’ll find many reputable programs who know how to fix this Outlook issue.
How to Reduce a PST File Size
To prevent frequent corruption, you can routinely reduce your PST file size.
- In Outlook, empty the Deleted Items folder.
- Select File and go to Account Settings.
- On the Data Files tab, click the data file you want to compact, and then click Settings.
- Note: If you have an Exchange or Outlook.com email account, click the Advanced tab and then go to Outlook Data File Settings.
- A dialogue box will appear; click Compact Now and then OK.
How to Restore a Deleted PST File
Let’s eliminate any feelings of despair regarding a deleted file. There’s often an opportunity to recover it. If you cannot restore the file from your computer’s recycling bin, here’s what to do:
How to Restore a PST file that’s been permanently deleted:
- Type C:UsersUserNameDocumentsOutlook Files (replacing “UserName” with your name) into the search bar of your computer.
- Then right-click on Outlook Files.
- Select “Restore Previous Versions.”
- Choose a version to restore from the tab.
Switching to Mailbird
We recently surveyed 287 of our users to ask, “What made you try Mailbird in the first place?” Nearly 40% moved to Mailbird specifically because of bugs or support issues with their other email clients, 17% of which specifically called out Outlook.
A desktop client can do several things to make your day more productive. Having to learn how to fix Outlook issues because of endless technical glitches makes us sad. Mostly because this doesn’t line up with Mailbird’s ultimate vision: to create a healthy relationship with email for everyone.
Here are a few features we love that could help you navigate your inbox stress-free.
- Simple: Mailbird supports all email providers with IMAP configuration (even Outlook), setup is quick, and you can customize our layout however you’d like.
- Unified Inbox: You can stay organized with tabs to view your inboxes separately but also see all of your emails in one place.
- Snooze: This is a great feature if you have a series of emails to get to when you can, but not right now. Hit the Snooze button on your emails and tell the inbox exactly when to bring those emails back to the top of your list.
- Free 24/7 Email Support: If you have any issues with setting up an email account or integrating one of the apps we support, we’re eagerly awaiting your message.
- Speed Reader: This super cool tool will present your email to you in such a way that you can read it three times faster than usual. It’s great for bulky emails where you just need to get the main idea.
- Plenty of Integrations: Mailbird has a library of apps you can integrate into your client to help you manage the rest of your tasks. You can send messages to Slack, WhatsApp, and Facebook Messenger, send files to Drobox, collaborate on Trello, sign forms with FormSwift, and much more.
These are just a few ways we make email easier. If you’re curious to get started, we recommend downloading our 14-day free trial. Our support team is available to chat with you about how to effortlessly transfer your Outlook to Mailbird any time.
