Outlook account keeps getting Authentication Error

Mailspring-Team, could you please fix this Bug or give a workaround?
Thank you

For everybody that’s using MailSpring as an outlook replacment:

Both microsoft and google are doing everything they can to destroy small open source alternative. Mailspring is a small open source application where the support for things will always be slow and right now both outlook accounts and gmail accounts are only temporary working (outlook with app password that microsoft is deprecating for no real reason since everybody even google and apple still support it, and google too since the oauth 2.0 login is not working and you can only use imap to log in).

FairEmail on Android is working great but there is no desktop version.

So I had to replace MailSpring with Thunderbird.

Thunderbird is still open source but so big that changes like the one made by google and microsoft are quick to be implemented.

The main problem of Thunderbird is the first configuration, it’s not easy at all if you got a lot to take care of like me.

So I suggest to change but gradually (not like I did in a day because it will take you all day).

I will post below a couples of problems-solutions that I had to face:

  1. Thunderbird support for exchange is not complete if you are not using owl (a paid extension). It is usually not a problem if you just want the emails since you can use imap with oauth 2.0 support but since Thunderbird will not suggest email addresses based on sent/inbox items you will need to export the contact list from outlook. You can do it from the web app of outlook only if your contact list is a regular contact list, if you are looking at shared contacts you first need to install outlook 365 (not the “new outlook”, the one that come with the office suite, that should not be a problem if your organization is using it since they will automatically use that license). From outlook 365 you need to go to the “person” tab and go on one of the shared contacts function (the one where you can organize, not the one where you can search), click on A: and select all, right click, add to contacts.

Once it will finish (it will take a while and it can freeze your pc) use outlook web to export the list in csv (the csv list from outlook 365 is broken and will not import properly). When you import take a momento to actually map name/surname/email properly since they can be different.

Once you got that right you can activate the “add automatically to address book function when you write to new email address” to keep the list updated. This was the most difficult thing to solve. Once everything is done you will not need outlook 365 on your pc anymore and, if you are not using it, you will be able to uninstall also the other office suite apps. Keep in mind that if you got a PC where outlook 365 is already installed for work you can use that to do the trick to import/export the contacts (I got a pc but the email is from a different company that’s why I had to do it like that).

  1. You can use HTML to make your signature and use images that will not be blocked too if you include them base64. The main difference is that mailspring offer a preview while thunderbird will not. Take this as an example:
Name LastName
What you do

you can use this website instead to preview:

  1. Thunderbird if you are not english will mistmatch a lot of folder (icloud will be a mess), just right click on the email account and subscribe… to the correct folders (make sure to have an example email in every folders). This was an easy fix but not something that I had to face anywhere else.

  2. Thunderbird will not start at startup and will not minimize by default. win+R->shell:startup->copy a shortcut of thunderbird there.

Install Minimize on startup extension, activate “When Thunderbird is minimized, move it to the tray” setting.

  1. Add “Dark Reader” extension for a dark mode inside the emails.

  2. Unified inbox is not on by default, right click on the top to activate menu bar->View->Folders->Unified Folders, you can put it on top too, just use the 3 dots.

  3. On first startup Outlook will open a “startup page”, you can deactivate it. Just remember that’s also the preview for mails. I closed it first and I was only able to open emails in another tab with double click… You can reopen it of course.

There are a lot of settings that you will have to learn again, take your time.

Once done thunderbird is not actually bad, but there is a lot to configure at the beginning compared to Mailspring, and the fact that does not suggest emails based on received/sent already existing emails is something that most other clients support and the reason why address books was not an easy task (that I did not had to do with Mailspring and FairEmail). The signature was difficult everywhere since only outlook/the old not supported mail for windows 10 support copy&paste from office for the images but once done is not difficult. The subscribe to the wrong folders is a problem with Thunderbird, but once corrected is a one time thing. Again the startup thing is a one time configuration, same deal with dark reader and the startup page and the unified inbox.

So basically there are a lot of basic configurations to make the first time and once done you should be able to use it without any issue.

If you want full exchange support (not sure who will need it) Thunderbird will support it in the future (Adventures In Rust: Bringing Exchange Support To Thunderbird you can see why mails already work and address book and calendar will be there soon) and the paid exension (10€ each year) offer it today.

In the end I’m still glad I switched but I did use the wrong program and I’m sorry to say I suggested the wrong program too… Mailspring is amazing and got an amazing interface but the support is not enough for a lot of people

2 Likes

This app password worked for me. I’m not on 365 either but have my 2fa on and “Passwordless account” OFF. Hopefully it will last.
Scroll down on this page after logging in:
https://account.live.com/proofs/Manage/additional
To 3rd section down: “App passwords”
1st option is [Create a new app password]
copy the new PSWD
Open Mailspring Preferences/accounts tab/Click on MS acct. then on right column
"Update connection Settings " gives you place to paste in new password
and paste

App passwords

Some apps and devices (such as Xbox 360, Windows Phone, or mail apps on your other devices) don’t support security codes for two-step verification. In these cases, you need to create an app password to sign in. Learn more about app passwords.

Create a new app password

Just remove the OutLook/HotMail account from MailSpring, create a new App password with 2FA on, wait for like 10 minutes and add the account back with the new App password. It should work. I believe it is something on the MS end activating the App password or something like that.

I enabled 2FA and created an app password, and still no dice. :frowning:

Checking the logs, it is connecting and sending the username and password across just fine, but then the server immediately replies with 2 NO LOGIN failed..

In my case, I believe it’s because my email uses a custom domain for my org and microsoft limits these cases to POP which mailspring doesn’t support. Just info in case this is the issue for others

Here’s their article
scroll down to the bottom of the IMAP connection errors dropdown

Hmm interesting. I’m using a custom domain as well. But I know that IMAP for this particular account was working in Mailspring previously.

Maybe it’s a recent change by Microsoft then? Seems weird to go back to POP though. Possibly a way to test if it’s limiting you to POP or not:

sign into outlook online
click settings in the top right then Mail → Sync email then under POP and IMAP I only see an option to “let devices and apps use POP”. From the site I previously send it seems like there should be a separate option for IMAP as well.

Just a heads up, this issue should be fixed in a few days!