Different SMTP for each Company

F15Eagle · June 5, 2025, 10:01pm

Version 5.9.4 C160
Environment: Ubuntu Server - un-tared TAR file and set up directly on host OS

I just discovered that on company B, none of my clients paid because both companies use the same SMTP email address. Company B customers were expecting emails from the domain corresponding to Company B, not Company A and probably thought it was spam. I have different domains and SMTP servers for Company A and B.

I saw this was asked for back in 2016. Is there currently a way to have Company A and Company B use different SMTP server configs?

Thank you.

hillel · June 6, 2025, 5:04am

Hi,

In the latest version of the app you can configure the SMTP settings on Settings > Email Settings.

F15Eagle · June 7, 2025, 6:10am

Thank you. I don’t think I have the latest version (v5.9.4-C160) but I found Settings → Email. I went to company B, modified the SMTP user account but it still seems to be sending from the 1st company’s email account. Specifically, both companies send from the same SMTP user account but the friendly name received in test email shows Company A or Company B. It seems that it uses the same email account for both companies.

hillel · June 7, 2025, 5:59pm

I suggest testing with the latest version of the app.

InvoiceHorst · June 7, 2025, 8:24pm

maybe you use in your config (docker config.yaml maybe?) the mail setup… remove the mail infos from the config file and use the mail settings from the homepage > settings >email settings… this works for me fine… (i use docker)

F15Eagle · June 7, 2025, 10:14pm

I now have the latest version and the same behavior persists.

F15Eagle · June 7, 2025, 10:16pm

I’m not using docker. I used composer to download it, which I believe is a one time thing? I checked the .env file but I found no email server references. Are there any other config files?

hillel · June 8, 2025, 5:12am

Have you configured SMTP settings in the app for both companies?

F15Eagle · June 8, 2025, 5:04pm

I do not use the applications. I only use the web UI.

hillel · June 8, 2025, 5:09pm

By ‘app’ I meant ‘web app’

Have you configured settings for both companies?

You may also want to try removing the .env settings

F15Eagle · June 14, 2025, 8:23pm

Yes, I have specified unique settings for both companies.

I tried renaming the .env file to .env.bak, then I restarted nginx.

The website shows:

500 — Server Error
Check storage/logs for more details

This is the recent part of the log:

[2025-06-14 19:53:20] production.ERROR: No application encryption key has been specified. {"exception":"[object] (Illuminate\\Encryption\\MissingAppKeyException(code: 0): No application encryption key has been specified. at /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Encryption/EncryptionServiceProvider.php:83)
[stacktrace]
#0 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Support/helpers.php(399): Illuminate\\Encryption\\EncryptionServiceProvider->Illuminate\\Encryption\\{closure}()
#1 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Encryption/EncryptionServiceProvider.php(81): tap()
#2 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Encryption/EncryptionServiceProvider.php(64): Illuminate\\Encryption\\EncryptionServiceProvider->key()
#3 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Encryption/EncryptionServiceProvider.php(32): Illuminate\\Encryption\\EncryptionServiceProvider->parseKey()
#4 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(952): Illuminate\\Encryption\\EncryptionServiceProvider->Illuminate\\Encryption\\{closure}()
#5 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(832): Illuminate\\Container\\Container->build()
#6 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Application.php(1078): Illuminate\\Container\\Container->resolve()
#7 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(763): Illuminate\\Foundation\\Application->resolve()
#8 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Application.php(1058): Illuminate\\Container\\Container->make()
#9 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(1133): Illuminate\\Foundation\\Application->make()
#10 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(1043): Illuminate\\Container\\Container->resolveClass()
#11 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(994): Illuminate\\Container\\Container->resolveDependencies()
#12 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(832): Illuminate\\Container\\Container->build()
#13 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Application.php(1078): Illuminate\\Container\\Container->resolve()
#14 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(763): Illuminate\\Foundation\\Application->resolve()
#15 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Application.php(1058): Illuminate\\Container\\Container->make()
#16 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(198): Illuminate\\Foundation\\Application->make()
#17 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(127): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#18 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Routing/Router.php(807): Illuminate\\Pipeline\\Pipeline->then()
#19 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Routing/Router.php(786): Illuminate\\Routing\\Router->runRouteWithinStack()
#20 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Routing/Router.php(750): Illuminate\\Routing\\Router->runRoute()
#21 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Routing/Router.php(739): Illuminate\\Routing\\Router->dispatchToRoute()
#22 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Kernel.php(201): Illuminate\\Routing\\Router->dispatch()
#23 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(170): Illuminate\\Foundation\\Http\\Kernel->Illuminate\\Foundation\\Http\\{closure}()
#24 /usr/share/nginx/invoiceninja/vendor/sentry/sentry-laravel/src/Sentry/Laravel/Http/FlushEventsMiddleware.php(13): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#25 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Sentry\\Laravel\\Http\\FlushEventsMiddleware->handle()
#26 /usr/share/nginx/invoiceninja/vendor/sentry/sentry-laravel/src/Sentry/Laravel/Http/SetRequestIpMiddleware.php(45): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#27 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Sentry\\Laravel\\Http\\SetRequestIpMiddleware->handle()
#28 /usr/share/nginx/invoiceninja/vendor/sentry/sentry-laravel/src/Sentry/Laravel/Http/SetRequestMiddleware.php(31): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#29 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Sentry\\Laravel\\Http\\SetRequestMiddleware->handle()
#30 /usr/share/nginx/invoiceninja/vendor/livewire/livewire/src/Features/SupportDisablingBackButtonCache/DisableBackButtonCacheMiddleware.php(19): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#31 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Livewire\\Features\\SupportDisablingBackButtonCache\\DisableBackButtonCacheMiddleware->handle()
#32 /usr/share/nginx/invoiceninja/app/Http/Middleware/Cors.php(24): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#33 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): App\\Http\\Middleware\\Cors->handle()
#34 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Http/Middleware/TrustProxies.php(58): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#35 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Illuminate\\Http\\Middleware\\TrustProxies->handle()
#36 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/TransformsRequest.php(21): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#37 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/ConvertEmptyStringsToNull.php(31): Illuminate\\Foundation\\Http\\Middleware\\TransformsRequest->handle()
#38 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Illuminate\\Foundation\\Http\\Middleware\\ConvertEmptyStringsToNull->handle()
#39 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/TransformsRequest.php(21): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#40 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/TrimStrings.php(51): Illuminate\\Foundation\\Http\\Middleware\\TransformsRequest->handle()
#41 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Illuminate\\Foundation\\Http\\Middleware\\TrimStrings->handle()
#42 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Http/Middleware/ValidatePostSize.php(27): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#43 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Illuminate\\Http\\Middleware\\ValidatePostSize->handle()
#44 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/PreventRequestsDuringMaintenance.php(110): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#45 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Illuminate\\Foundation\\Http\\Middleware\\PreventRequestsDuringMaintenance->handle()
#46 /usr/share/nginx/invoiceninja/vendor/sentry/sentry-laravel/src/Sentry/Laravel/Tracing/Middleware.php(79): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#47 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(209): Sentry\\Laravel\\Tracing\\Middleware->handle()
#48 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(127): Illuminate\\Pipeline\\Pipeline->Illuminate\\Pipeline\\{closure}()
#49 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Kernel.php(176): Illuminate\\Pipeline\\Pipeline->then()
#50 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Kernel.php(145): Illuminate\\Foundation\\Http\\Kernel->sendRequestThroughRouter()
#51 /usr/share/nginx/invoiceninja/public/index.php(56): Illuminate\\Foundation\\Http\\Kernel->handle()
#52 {main}
"} 
[2025-06-14 19:53:20] production.INFO: To setup the app run: cp .env.example .env  
[2025-06-14 19:53:20] production.ERROR: No application encryption key has been specified. {"exception":"[object] (Illuminate\\Encryption\\MissingAppKeyException(code: 0): No application encryption key has been specified. at /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Encryption/EncryptionServiceProvider.php:83)
[stacktrace]
#0 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Support/helpers.php(399): Illuminate\\Encryption\\EncryptionServiceProvider->Illuminate\\Encryption\\{closure}()
#1 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Encryption/EncryptionServiceProvider.php(81): tap()
#2 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Encryption/EncryptionServiceProvider.php(64): Illuminate\\Encryption\\EncryptionServiceProvider->key()
#3 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Encryption/EncryptionServiceProvider.php(32): Illuminate\\Encryption\\EncryptionServiceProvider->parseKey()
#4 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(952): Illuminate\\Encryption\\EncryptionServiceProvider->Illuminate\\Encryption\\{closure}()
#5 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(832): Illuminate\\Container\\Container->build()
#6 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Application.php(1078): Illuminate\\Container\\Container->resolve()
#7 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(763): Illuminate\\Foundation\\Application->resolve()
#8 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Application.php(1058): Illuminate\\Container\\Container->make()
#9 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(1133): Illuminate\\Foundation\\Application->make()
#10 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(1043): Illuminate\\Container\\Container->resolveClass()
#11 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(994): Illuminate\\Container\\Container->resolveDependencies()
#12 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(832): Illuminate\\Container\\Container->build()
#13 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Application.php(1078): Illuminate\\Container\\Container->resolve()
#14 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Container/Container.php(763): Illuminate\\Foundation\\Application->resolve()
#15 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Application.php(1058): Illuminate\\Container\\Container->make()
#16 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Kernel.php(258): Illuminate\\Foundation\\Application->make()
#17 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Http/Kernel.php(216): Illuminate\\Foundation\\Http\\Kernel->terminateMiddleware()
#18 /usr/share/nginx/invoiceninja/public/index.php(63): Illuminate\\Foundation\\Http\\Kernel->terminate()
#19 {main}
"} 
[2025-06-14 19:53:20] production.INFO: To setup the app run: cp .env.example .env  
[2025-06-14 19:53:21] production.ERROR: Uncaught ErrorException: Cannot modify header information - headers already sent by (output started at /usr/share/nginx/invoiceninja/vendor/symfony/http-foundation/Response.php:387) in /usr/share/nginx/invoiceninja/vendor/symfony/http-foundation/Response.php:322
Stack trace:
#0 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Bootstrap/HandleExceptions.php(256): Illuminate\Foundation\Bootstrap\HandleExceptions->handleError()
#1 [internal function]: Illuminate\Foundation\Bootstrap\HandleExceptions->Illuminate\Foundation\Bootstrap\{closure}()
#2 /usr/share/nginx/invoiceninja/vendor/symfony/http-foundation/Response.php(322): header()
#3 /usr/share/nginx/invoiceninja/vendor/symfony/http-foundation/Response.php(401): Symfony\Component\HttpFoundation\Response->sendHeaders()
#4 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Bootstrap/HandleExceptions.php(219): Symfony\Component\HttpFoundation\Response->send()
#5 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Bootstrap/HandleExceptions.php(196): Illuminate\Foundation\Bootstrap\HandleExceptions->renderHttpResponse()
#6 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Bootstrap/HandleExceptions.php(256): Illuminate\Foundation\Bootstrap\HandleExceptions->handleException()
#7 [internal function]: Illuminate\Foundation\Bootstrap\HandleExceptions->Illuminate\Foundation\Bootstrap\{closure}()
#8 {main}
  thrown {"exception":"[object] (Symfony\\Component\\ErrorHandler\\Error\\FatalError(code: 0): Uncaught ErrorException: Cannot modify header information - headers already sent by (output started at /usr/share/nginx/invoiceninja/vendor/symfony/http-foundation/Response.php:387) in /usr/share/nginx/invoiceninja/vendor/symfony/http-foundation/Response.php:322
Stack trace:
#0 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Bootstrap/HandleExceptions.php(256): Illuminate\\Foundation\\Bootstrap\\HandleExceptions->handleError()
#1 [internal function]: Illuminate\\Foundation\\Bootstrap\\HandleExceptions->Illuminate\\Foundation\\Bootstrap\\{closure}()
#2 /usr/share/nginx/invoiceninja/vendor/symfony/http-foundation/Response.php(322): header()
#3 /usr/share/nginx/invoiceninja/vendor/symfony/http-foundation/Response.php(401): Symfony\\Component\\HttpFoundation\\Response->sendHeaders()
#4 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Bootstrap/HandleExceptions.php(219): Symfony\\Component\\HttpFoundation\\Response->send()
#5 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Bootstrap/HandleExceptions.php(196): Illuminate\\Foundation\\Bootstrap\\HandleExceptions->renderHttpResponse()
#6 /usr/share/nginx/invoiceninja/vendor/laravel/framework/src/Illuminate/Foundation/Bootstrap/HandleExceptions.php(256): Illuminate\\Foundation\\Bootstrap\\HandleExceptions->handleException()
#7 [internal function]: Illuminate\\Foundation\\Bootstrap\\HandleExceptions->Illuminate\\Foundation\\Bootstrap\\{closure}()
#8 {main}
  thrown at /usr/share/nginx/invoiceninja/vendor/symfony/http-foundation/Response.php:322)
[stacktrace]
#0 {main}
"}

I then restored the .env file. I edited out all the email lines, which were populated with “” anyways (empty).

Then I went into the website, noticed at the top there was an icon for “Web App”. I went into that, which looks different than the web GUI I’m used to. I went to settings and specified SMTP Server B which corresponds to Company B.

Unfortunately, after all this, Company B still sends emails from the email server specified by Company A.

F15Eagle · June 14, 2025, 8:34pm

Also, I updated to v5.12.1 from within the GUI and the problem persists.

hillel · June 14, 2025, 8:59pm

@david do you have any suggestions?

david · June 14, 2025, 10:00pm

Sounds like a configuration of issues