Ricoh “Authentication with the destination has failed”

Authentication with the destination has failed. Check settings. To check the current status, press [Scanned Files Status].

What Ricoh says

Ricoh's instructions give one cause: “The entered user name or password was invalid.” Its knowledge base says the same: the user name or password you set may not be correct. Ricoh's fix:

• “Check that the user name and password are correct.”
• “Check that the ID and password for the destination folder are correct.”
• “A password of 128 or more characters may not be recognized.”

The same message appears for scan to folder, which is why Ricoh mentions the destination folder's ID and password. For scan to email, the user name and password are the ones in the Ricoh's SMTP authentication settings.

Sources: Ricoh, When data transmission fails; Ricoh, “Authentication with the destination has failed.” is displayed (read October 30, 2026)

When the mail server is Microsoft 365

If the Ricoh's SMTP server is smtp.office365.com and it signs in with a mailbox's email address and password, it uses what Microsoft calls SMTP AUTH. Microsoft 365 can refuse that sign-in even when the password is correct. For printers and scanners whose sign-in fails, Microsoft's troubleshooting article says to check:

1. SMTP AUTH is enabled on the licensed mailbox the Ricoh uses.
2. Multifactor authentication on that mailbox.
3. Security defaults in Microsoft Entra ID.
4. A Conditional Access policy that blocks legacy authentication.

Microsoft's exact steps for each are on 535 5.7.3: Microsoft's four checks, and turning on SMTP AUTH for one mailbox is on how to enable SMTP AUTH.

Sources: Microsoft Learn, Fix issues with printers, scanners, and LOB apps that send email using Microsoft 365; Microsoft Learn, How to set up a multifunction device or application to send email using Microsoft 365 or Office 365; Microsoft 365 Message Center notice MC786329 (updated January 27, 2026) (read October 30, 2026)

Ricoh's OAuth 2.0 route

Ricoh supports Microsoft's OAuth sign-in on models with updated firmware. From Ricoh's notice:

“To send email using OAuth2.0 authentication, you must first update to a firmware version that supports OAuth2.0 authentication, then specify necessary settings from Web Image Monitor.”Ricoh, Update: Impact of Microsoft basic authentication deprecation in Exchange Online and support for affected Ricoh products

Ricoh's setup, in its own words:

• “Select OAuth 2.0 as the authentication method for sending email.”
• “Set the SMTP server to "smtp.office365.com," and enter the email address of your Exchange Online account as both the email address and user name for authentication.”
• “To use OAuth2.0 authentication with the updated firmware, you must also specify an administrator email address.”

Ricoh's notice lists each supported model with its minimum firmware version. Until firmware is available, Ricoh's advice is: “Until firmware for OAuth2.0 authentication is available for your product, we recommend switching to methods that do not rely on email transition or using email services other than Exchange Online.” Our Ricoh scan to email page has the details.

Sources: Ricoh, Update: Impact of Microsoft basic authentication deprecation in Exchange Online and support for affected Ricoh products; Ricoh, How to Scan to Email with Microsoft Exchange Online OAuth 2.0 Authentication (read October 30, 2026)

“Transmission has failed.”

A different message, with a different cause in Ricoh's instructions:

Transmission has failed. To check the current status, press [Scanned Files Status].

Ricoh: “While a file was being sent, a network error occurred and the file could not be sent correctly.” And: “If the same message appears again after scanning again, the cause could be a mixed network, or else network settings were changed during WSD scanner transmission. For details about network error, contact your administrator.”

Source: Ricoh, When data transmission fails (read October 30, 2026)

Fixes that last past December 2026

A Ricoh that signs in to Microsoft 365 with a password needs one of these before Microsoft turns password sign-in off by default:

• OAuth on the device. SMTP AUTH supports OAuth as well as passwords, and it's the method Microsoft recommends. It works if your copier's maker supports it on your model and firmware: see the guide and your brand's page.
• An SMTP relay connector. The device sends to your MX endpoint on port 25, and Microsoft 365 recognises it by your static IP address or a certificate. Steps.
• Direct Send or High Volume Email, if scans only ever go to people inside your organization. Details.
• A third-party relay, which Microsoft's notice names for anything that must keep a username and password: “if you must use Basic auth to send email with Exchange Online, then you must use one of the alternatives or a 3P solution.”

Common questions