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Upgrade to Reckon Desktop v35 has broken email via gmail and Outlook cannot be setup for gmail

Tuntable

@Rav Hello and hope you can help. I have 400 invoices to send out and email via gmail suddenly doesn't work after upgrading to v35.
I have set Reckon to use Outlook Classic V2 as instructed. I have tried to configure Outlook to handle the gmail account, but cannot set it up. I can start to set up the account in Outlook and get to the step where Microsoft needs my permission to access certain information. The process fails at this point with "Sorry, we could not sign you into google-IMAP".
I have spent several hours trying to get past this, but haven't found a solution. It seems that Outlook Classic and Google are at odds.

Can you help?

Helen

Accepted answers

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Lucas Andrews

Hi @Tuntable,

Thank you for reaching out to the community.

It's going to be a little difficult to troubleshoot as we don't support Outlook as a software and you may need to contact Microsoft instead to see if they can assist with adding an external account.

Once the accounts setup, everything should go smoothly and you will be able to email out from Reckon Accounts Desktop.

Rav

Hi @Tuntable

Were you previously using this Gmail account with Outlook and the previous version of Reckon Accounts (v34)? ie. has this only just started since you upgraded to the latest 2026 v35 edition?

… get to the step where Microsoft needs my permission to access certain information.

You've mentioned it fails once its gets to the above step. What does that look like exactly and are you granting access to the info being requested?

Tuntable

Hello @Rav, No I haven't used Outlook with Gmail previously as Reckon interfaced directly.
The failed step comes after configuring Outlook 2019 which gives a popup to log into the gmail account using the normal password. If the password is accepted, then there is another window that asks me to give permission for Microsoft to get information from Google. I approve this request and it always fails with the message "Sorry, we could not sign you into google-IMAP".

Tuntable

@Rav I've just got things working. Since I've been unable to add my workspace gmail account to Outlook 2019 directly (which is the required Classic version) I've installed GWSMO (Google Workspace Sync for Microsoft Outlook). It seems to bypass all the security failures that Google encounters with Outlook during the setup. I now have an Outlook that is syncing all the workspace emails and that Reckon will talk to for sending emails out.
I now need to find a way to stop it synching loads of emails and only accept Reckon outgoing emails to pass on.
Leaving this here for anyone else who has the same issue.

Thanks for being willing to help @Rav. Always appreciated :)

Tuntable

@Rav - sorry missed your other question. Yes this is an issue since upgrading to v35 last week - H

CYML

Hi,

I'm having exactly the same problem.

I updated to v35 a few days ago and have been having issues with sending emails from Reckon using a Gmail address.

Prior to v34, I was sending emails using an old Outlook.

After the update to v34, I could no longer use the Gmail address with Outlook when Google stopped allowing access to "less secure apps".

https://support.google.com/accounts/answer/6010255?hl=en

I somehow managed to bypass Outlook to keep using the same Gmail address with a Google App Password though.

But after updating to v35, the method doesn't work anymore.

I tried changing the settings in Reckon according to this article: https://help.reckon.com/article/ddvbx3xe6s-changes-with-email-integration-options-in-reckon-accounts-desktop.

Outlook (Classic) wouldn't work because my old Outlook is a "less secure app" to Google.

Outlook (Classic) v2 is crashing my Reckon. These are the error messages.

Anyone able to shed some light please ? Thanks.

Tuntable

Hello @CYML, I'm not sure if the workaround that I found will work for you. My gmail address is part of a Google workspace account.
I've installed GWSMO (Google Workspace Sync for Microsoft Outlook). It
seems to bypass all the security failures that Google encounters with
Outlook during the setup. I now have an Outlook that is syncing all the
workspace emails and that Reckon will talk to for sending emails out.

CYML

Thanks @Tuntable for the suggestion. Unfortunately we don't have a Google Workspace account to use GWSMO. I'm hoping there's another workaround for this problem.

Tuntable

ok @CYML, I've just set up another gmail (not workspace) account in Outlook. What worked was setting the google account to 2FA and generating a special 16 digit App Password to use with Outlook. Getting that new password into Outlook was tricky. The "Repair" process to provide the new password didn't work. I used the Control Panel method. See pic. Best of luck :)

CYML

Appreciate your help @Tuntable 😊

With the help from AI, I managed to reconfigure my old Outlook to connect to my Gmail account using the Google App Password.

So Reckon Accounts is talking to Outlook, and Outlook is talking to Gmail. It seems to be working fine now.

Hopefully this post will be helpful to others who come across the same issue.

Tuntable

Awesome and good to know. There will be others, I'm sure of it!

Lynne_8946547

I'm having a similar issue, but with sending payslips.

I cannot send any payslips, no matter what type of email they use.

I upgraded to v35 today and thought I would test it as I had seen this thread.

It didn't work. Attached is the error message I got.

I've always used Outlook classic with Reckon and never had an issue until now.

I'm not keen on the work arounds given above and was wondering if Reckon knew why this has suddenly happened.

Regards

Lynne