Office365 POP3 Authenticate Fails but Previously Succeeded

June 15, 2023

Office365 POP3 Authenticate Fails but Previously Succeeded

It’s normal for OAuth2 access tokens to expire after some time, such as 1 hour, and then you’ll need to refresh and retry.

For example, this error in the LastErrorText for a call to Pop3Authenticate could indicate the OAuth2 accces token expired:

Pop3Authenticate:
    DllDate: Mar 28 2023
    ChilkatVersion: 9.5.0.94
    UnlockPrefix: ***
    Architecture: Little Endian; 32-bit
    Language: ActiveX
    VerboseLogging: 1
    Pop3Authenticate:
        username: ***
        popSPA: 0
        greeting: +OK The Microsoft Exchange POP3 service is ready. [***]
        pop_office365_xoauth2:
            PopCmdSent: AUTH XOAUTH2
            PopCmdResp: +
            auth_xoauth2_response_1: +
            PopCmdSent: 
            PopCmdResp: -ERR Authentication failure: unknown user name or bad password.
            POP3 response indicates failure.
            AUTH_XOAUTH2_response: -ERR Authentication failure: unknown user name or bad password.
            (leaveContext 1750ms)
        POP3 authentication failed
       (leaveContext 1750ms)
    Failed.
    (leaveContext 1750ms)

To auto-refresh the OAuth2 access token and retry, see:

The duration of OAuth2 access tokens can vary depending on the implementation and the specific requirements of the authorization server. In general, access tokens have an expiration time, known as the token’s “lifetime” or “expiration time,” which is set by the authorization server when issuing the token. The client application can use the access token until it expires.

The expiration time is typically included in the token response from the authorization server as the “expires_in” parameter or as an “expires_at” timestamp. This value represents the number of seconds or an absolute time in the future when the token will expire.

The actual token lifetime can vary based on the security and usage requirements of the application and the authorization server’s configuration. It can range from a few minutes to several hours or even longer. Shorter token lifetimes enhance security by minimizing the window of opportunity for unauthorized access, while longer lifetimes can improve performance and user experience by reducing the frequency of token refreshes.

To continue accessing protected resources beyond the token’s expiration, the client application needs to obtain a new access token by using a refresh token, if one was issued during the initial authorization process. The refresh token allows the client to request a new access token without involving the user in the authorization flow again. The lifetime of refresh tokens is typically much much longer than that of access tokens.

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Office365 POP3 Authenticate Fails but Previously Succeeded

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