Emailing Invoices to Local Email Works, to External Email Does Not Work

Emailing invoices to Local Email Works, but the same invoices to External Email Does Not Work.

Seems that this issue started this month, January 2022. For December 2021 and before, the invoices that were manually created and via Recurring Invoices were emailed to external addresses just fine. For many months prior, Recurring Invoices emailed properly to local and external email addresses.

We continue receive the CC’d notifications that the invoices have been emailed properly as have always. Now, if an invoice is sent to an internal email it goes fine but to an external email, it appears to go but actually does not. We can send email directly and successfully to the external email using webmail and an email client such as Thunderbird using the same mail server as configured with Invoice Ninja. So, email is actually reaching the external email addresses fine except through Invoice Ninja.

We’ve updated Invoice Ninja to 4.5.47 on a production and test installation and the issue persists. Our PHP version has remained 7.3 during this entire time frame. Using the same hosting server but on a different Invoice Ninja install, we get the same results. Sending messages from the same host server as the Invoice Ninja installation reaches external email addresses successfully. Any advice to help identify the issue?

Hi,

I would assume it’s more likely an email issue than a problem with the app.

@david do you have any ideas?

Seems that our email servers are working as intended. Via Invoice Ninja, we seem to hit a road block. Are there some tests that Invoice Ninja perform to validate outgoing email?

Additional Tests:

RESULTS for LOCAL Enabled via Invoice Ninja:
Send NOT successful to HOTMAIL address.
Send NOT successful to GMAIL address.
Send successful to LOCAL address.

RESULTS for HOTMAIL Enabled via Invoice Ninja:
Send successful to HOTMAIL address.
Send NOT successful to GMAIL address.
Send successful to LOCAL address.

RESULTS for GMAIL Enabled via Invoice Ninja:
Send successful to HOTMAIL address.
Send successful to GMAIL address.
Send successful to LOCAL address.

RESULTS for Manual Email Using Mail Client:
Send successful to HOTMAIL address.
Send successful to GMAIL address.
Send successful to LOCAL address.

Not that I’m aware of

The info here may help to get email working with Gmail

@hillel Thank you for that reply regarding GMAIL, however I confirm these are the settings I am using with one exception, change the From Name to match email address too and decrease my Google account’s security.

Driver - SMTP
From Name - GMAIL-email-address
From Address - GMAIL-email-address
Username - GMAIL-email-address
Host - smtp.gmail.com
Port - 587
Encryption - TLS
Password - {password}

====================================

Had to be sure to authorize the app for GMail use by lowering security in my Google account:
Allow less secure apps: ON

Updated RESULTS.

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@hillel My follow-up response and resolution. (Though not ideal based on my goal.)

I am still not sure exactly what has happened as of yet, but I could no longer use our internally hosted email server nor our email gateway for email settings in the app. These servers are “external” to the server where the app is hosted.

SOLUTION: I created an email address on the same server that the app is installed, and applied the appropriate settings in the app.

Driver - SMTP
From Name - Vanity Name
From Address - localhost-email-address
Username - localhost-email-address
Host - localhost
Port - 25
Encryption - None
Password - {password}

RESULTS for LOCALHOST Enabled via Invoice Ninja:
Send successful to HOTMAIL address.
Send successful to GMAIL address.
Send successful to LOCAL address.

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