diff --git a/.ci/php-cs-fixer/composer.lock b/.ci/php-cs-fixer/composer.lock
index 01f3389111..f0dfaa1b19 100644
--- a/.ci/php-cs-fixer/composer.lock
+++ b/.ci/php-cs-fixer/composer.lock
@@ -744,23 +744,23 @@
         },
         {
             "name": "symfony/console",
-            "version": "v6.2.11",
+            "version": "v6.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/console.git",
-                "reference": "5aa03db8ef0a5457c316ec580e69562d97734c77"
+                "reference": "8788808b07cf0bdd6e4b7fdd23d8ddb1470c83b7"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/console/zipball/5aa03db8ef0a5457c316ec580e69562d97734c77",
-                "reference": "5aa03db8ef0a5457c316ec580e69562d97734c77",
+                "url": "https://api.github.com/repos/symfony/console/zipball/8788808b07cf0bdd6e4b7fdd23d8ddb1470c83b7",
+                "reference": "8788808b07cf0bdd6e4b7fdd23d8ddb1470c83b7",
                 "shasum": ""
             },
             "require": {
                 "php": ">=8.1",
-                "symfony/deprecation-contracts": "^2.1|^3",
+                "symfony/deprecation-contracts": "^2.5|^3",
                 "symfony/polyfill-mbstring": "~1.0",
-                "symfony/service-contracts": "^1.1|^2|^3",
+                "symfony/service-contracts": "^2.5|^3",
                 "symfony/string": "^5.4|^6.0"
             },
             "conflict": {
@@ -782,12 +782,6 @@
                 "symfony/process": "^5.4|^6.0",
                 "symfony/var-dumper": "^5.4|^6.0"
             },
-            "suggest": {
-                "psr/log": "For using the console logger",
-                "symfony/event-dispatcher": "",
-                "symfony/lock": "",
-                "symfony/process": ""
-            },
             "type": "library",
             "autoload": {
                 "psr-4": {
@@ -820,7 +814,7 @@
                 "terminal"
             ],
             "support": {
-                "source": "https://github.com/symfony/console/tree/v6.2.11"
+                "source": "https://github.com/symfony/console/tree/v6.3.0"
             },
             "funding": [
                 {
@@ -836,20 +830,20 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-05-26T08:16:21+00:00"
+            "time": "2023-05-29T12:49:39+00:00"
         },
         {
             "name": "symfony/deprecation-contracts",
-            "version": "v3.2.1",
+            "version": "v3.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/deprecation-contracts.git",
-                "reference": "e2d1534420bd723d0ef5aec58a22c5fe60ce6f5e"
+                "reference": "7c3aff79d10325257a001fcf92d991f24fc967cf"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/deprecation-contracts/zipball/e2d1534420bd723d0ef5aec58a22c5fe60ce6f5e",
-                "reference": "e2d1534420bd723d0ef5aec58a22c5fe60ce6f5e",
+                "url": "https://api.github.com/repos/symfony/deprecation-contracts/zipball/7c3aff79d10325257a001fcf92d991f24fc967cf",
+                "reference": "7c3aff79d10325257a001fcf92d991f24fc967cf",
                 "shasum": ""
             },
             "require": {
@@ -858,7 +852,7 @@
             "type": "library",
             "extra": {
                 "branch-alias": {
-                    "dev-main": "3.3-dev"
+                    "dev-main": "3.4-dev"
                 },
                 "thanks": {
                     "name": "symfony/contracts",
@@ -887,7 +881,7 @@
             "description": "A generic function and convention to trigger deprecation notices",
             "homepage": "https://symfony.com",
             "support": {
-                "source": "https://github.com/symfony/deprecation-contracts/tree/v3.2.1"
+                "source": "https://github.com/symfony/deprecation-contracts/tree/v3.3.0"
             },
             "funding": [
                 {
@@ -903,28 +897,29 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-03-01T10:25:55+00:00"
+            "time": "2023-05-23T14:45:45+00:00"
         },
         {
             "name": "symfony/event-dispatcher",
-            "version": "v6.2.8",
+            "version": "v6.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/event-dispatcher.git",
-                "reference": "04046f35fd7d72f9646e721fc2ecb8f9c67d3339"
+                "reference": "3af8ac1a3f98f6dbc55e10ae59c9e44bfc38dfaa"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/event-dispatcher/zipball/04046f35fd7d72f9646e721fc2ecb8f9c67d3339",
-                "reference": "04046f35fd7d72f9646e721fc2ecb8f9c67d3339",
+                "url": "https://api.github.com/repos/symfony/event-dispatcher/zipball/3af8ac1a3f98f6dbc55e10ae59c9e44bfc38dfaa",
+                "reference": "3af8ac1a3f98f6dbc55e10ae59c9e44bfc38dfaa",
                 "shasum": ""
             },
             "require": {
                 "php": ">=8.1",
-                "symfony/event-dispatcher-contracts": "^2|^3"
+                "symfony/event-dispatcher-contracts": "^2.5|^3"
             },
             "conflict": {
-                "symfony/dependency-injection": "<5.4"
+                "symfony/dependency-injection": "<5.4",
+                "symfony/service-contracts": "<2.5"
             },
             "provide": {
                 "psr/event-dispatcher-implementation": "1.0",
@@ -937,13 +932,9 @@
                 "symfony/error-handler": "^5.4|^6.0",
                 "symfony/expression-language": "^5.4|^6.0",
                 "symfony/http-foundation": "^5.4|^6.0",
-                "symfony/service-contracts": "^1.1|^2|^3",
+                "symfony/service-contracts": "^2.5|^3",
                 "symfony/stopwatch": "^5.4|^6.0"
             },
-            "suggest": {
-                "symfony/dependency-injection": "",
-                "symfony/http-kernel": ""
-            },
             "type": "library",
             "autoload": {
                 "psr-4": {
@@ -970,7 +961,7 @@
             "description": "Provides tools that allow your application components to communicate with each other by dispatching events and listening to them",
             "homepage": "https://symfony.com",
             "support": {
-                "source": "https://github.com/symfony/event-dispatcher/tree/v6.2.8"
+                "source": "https://github.com/symfony/event-dispatcher/tree/v6.3.0"
             },
             "funding": [
                 {
@@ -986,33 +977,30 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-03-20T16:06:02+00:00"
+            "time": "2023-04-21T14:41:17+00:00"
         },
         {
             "name": "symfony/event-dispatcher-contracts",
-            "version": "v3.2.1",
+            "version": "v3.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/event-dispatcher-contracts.git",
-                "reference": "0ad3b6f1e4e2da5690fefe075cd53a238646d8dd"
+                "reference": "a76aed96a42d2b521153fb382d418e30d18b59df"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/event-dispatcher-contracts/zipball/0ad3b6f1e4e2da5690fefe075cd53a238646d8dd",
-                "reference": "0ad3b6f1e4e2da5690fefe075cd53a238646d8dd",
+                "url": "https://api.github.com/repos/symfony/event-dispatcher-contracts/zipball/a76aed96a42d2b521153fb382d418e30d18b59df",
+                "reference": "a76aed96a42d2b521153fb382d418e30d18b59df",
                 "shasum": ""
             },
             "require": {
                 "php": ">=8.1",
                 "psr/event-dispatcher": "^1"
             },
-            "suggest": {
-                "symfony/event-dispatcher-implementation": ""
-            },
             "type": "library",
             "extra": {
                 "branch-alias": {
-                    "dev-main": "3.3-dev"
+                    "dev-main": "3.4-dev"
                 },
                 "thanks": {
                     "name": "symfony/contracts",
@@ -1049,7 +1037,7 @@
                 "standards"
             ],
             "support": {
-                "source": "https://github.com/symfony/event-dispatcher-contracts/tree/v3.2.1"
+                "source": "https://github.com/symfony/event-dispatcher-contracts/tree/v3.3.0"
             },
             "funding": [
                 {
@@ -1065,20 +1053,20 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-03-01T10:32:47+00:00"
+            "time": "2023-05-23T14:45:45+00:00"
         },
         {
             "name": "symfony/filesystem",
-            "version": "v6.2.10",
+            "version": "v6.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/filesystem.git",
-                "reference": "fd588debf7d1bc16a2c84b4b3b71145d9946b894"
+                "reference": "97b698e1d77d356304def77a8d0cd73090b359ea"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/filesystem/zipball/fd588debf7d1bc16a2c84b4b3b71145d9946b894",
-                "reference": "fd588debf7d1bc16a2c84b4b3b71145d9946b894",
+                "url": "https://api.github.com/repos/symfony/filesystem/zipball/97b698e1d77d356304def77a8d0cd73090b359ea",
+                "reference": "97b698e1d77d356304def77a8d0cd73090b359ea",
                 "shasum": ""
             },
             "require": {
@@ -1112,7 +1100,7 @@
             "description": "Provides basic utilities for the filesystem",
             "homepage": "https://symfony.com",
             "support": {
-                "source": "https://github.com/symfony/filesystem/tree/v6.2.10"
+                "source": "https://github.com/symfony/filesystem/tree/v6.3.0"
             },
             "funding": [
                 {
@@ -1128,20 +1116,20 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-04-18T13:46:08+00:00"
+            "time": "2023-05-30T17:12:32+00:00"
         },
         {
             "name": "symfony/finder",
-            "version": "v6.2.7",
+            "version": "v6.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/finder.git",
-                "reference": "20808dc6631aecafbe67c186af5dcb370be3a0eb"
+                "reference": "d9b01ba073c44cef617c7907ce2419f8d00d75e2"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/finder/zipball/20808dc6631aecafbe67c186af5dcb370be3a0eb",
-                "reference": "20808dc6631aecafbe67c186af5dcb370be3a0eb",
+                "url": "https://api.github.com/repos/symfony/finder/zipball/d9b01ba073c44cef617c7907ce2419f8d00d75e2",
+                "reference": "d9b01ba073c44cef617c7907ce2419f8d00d75e2",
                 "shasum": ""
             },
             "require": {
@@ -1176,7 +1164,7 @@
             "description": "Finds files and directories via an intuitive fluent interface",
             "homepage": "https://symfony.com",
             "support": {
-                "source": "https://github.com/symfony/finder/tree/v6.2.7"
+                "source": "https://github.com/symfony/finder/tree/v6.3.0"
             },
             "funding": [
                 {
@@ -1192,25 +1180,25 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-02-16T09:57:23+00:00"
+            "time": "2023-04-02T01:25:41+00:00"
         },
         {
             "name": "symfony/options-resolver",
-            "version": "v6.2.7",
+            "version": "v6.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/options-resolver.git",
-                "reference": "aa0e85b53bbb2b4951960efd61d295907eacd629"
+                "reference": "a10f19f5198d589d5c33333cffe98dc9820332dd"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/options-resolver/zipball/aa0e85b53bbb2b4951960efd61d295907eacd629",
-                "reference": "aa0e85b53bbb2b4951960efd61d295907eacd629",
+                "url": "https://api.github.com/repos/symfony/options-resolver/zipball/a10f19f5198d589d5c33333cffe98dc9820332dd",
+                "reference": "a10f19f5198d589d5c33333cffe98dc9820332dd",
                 "shasum": ""
             },
             "require": {
                 "php": ">=8.1",
-                "symfony/deprecation-contracts": "^2.1|^3"
+                "symfony/deprecation-contracts": "^2.5|^3"
             },
             "type": "library",
             "autoload": {
@@ -1243,7 +1231,7 @@
                 "options"
             ],
             "support": {
-                "source": "https://github.com/symfony/options-resolver/tree/v6.2.7"
+                "source": "https://github.com/symfony/options-resolver/tree/v6.3.0"
             },
             "funding": [
                 {
@@ -1259,7 +1247,7 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-02-14T08:44:56+00:00"
+            "time": "2023-05-12T14:21:09+00:00"
         },
         {
             "name": "symfony/polyfill-ctype",
@@ -1755,16 +1743,16 @@
         },
         {
             "name": "symfony/process",
-            "version": "v6.2.11",
+            "version": "v6.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/process.git",
-                "reference": "97ae9721bead9d1a39b5650e2f4b7834b93b539c"
+                "reference": "8741e3ed7fe2e91ec099e02446fb86667a0f1628"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/process/zipball/97ae9721bead9d1a39b5650e2f4b7834b93b539c",
-                "reference": "97ae9721bead9d1a39b5650e2f4b7834b93b539c",
+                "url": "https://api.github.com/repos/symfony/process/zipball/8741e3ed7fe2e91ec099e02446fb86667a0f1628",
+                "reference": "8741e3ed7fe2e91ec099e02446fb86667a0f1628",
                 "shasum": ""
             },
             "require": {
@@ -1796,7 +1784,7 @@
             "description": "Executes commands in sub-processes",
             "homepage": "https://symfony.com",
             "support": {
-                "source": "https://github.com/symfony/process/tree/v6.2.11"
+                "source": "https://github.com/symfony/process/tree/v6.3.0"
             },
             "funding": [
                 {
@@ -1812,20 +1800,20 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-05-19T07:42:48+00:00"
+            "time": "2023-05-19T08:06:44+00:00"
         },
         {
             "name": "symfony/service-contracts",
-            "version": "v3.2.1",
+            "version": "v3.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/service-contracts.git",
-                "reference": "a8c9cedf55f314f3a186041d19537303766df09a"
+                "reference": "40da9cc13ec349d9e4966ce18b5fbcd724ab10a4"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/service-contracts/zipball/a8c9cedf55f314f3a186041d19537303766df09a",
-                "reference": "a8c9cedf55f314f3a186041d19537303766df09a",
+                "url": "https://api.github.com/repos/symfony/service-contracts/zipball/40da9cc13ec349d9e4966ce18b5fbcd724ab10a4",
+                "reference": "40da9cc13ec349d9e4966ce18b5fbcd724ab10a4",
                 "shasum": ""
             },
             "require": {
@@ -1835,13 +1823,10 @@
             "conflict": {
                 "ext-psr": "<1.1|>=2"
             },
-            "suggest": {
-                "symfony/service-implementation": ""
-            },
             "type": "library",
             "extra": {
                 "branch-alias": {
-                    "dev-main": "3.3-dev"
+                    "dev-main": "3.4-dev"
                 },
                 "thanks": {
                     "name": "symfony/contracts",
@@ -1881,7 +1866,7 @@
                 "standards"
             ],
             "support": {
-                "source": "https://github.com/symfony/service-contracts/tree/v3.2.1"
+                "source": "https://github.com/symfony/service-contracts/tree/v3.3.0"
             },
             "funding": [
                 {
@@ -1897,25 +1882,25 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-03-01T10:32:47+00:00"
+            "time": "2023-05-23T14:45:45+00:00"
         },
         {
             "name": "symfony/stopwatch",
-            "version": "v6.2.7",
+            "version": "v6.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/stopwatch.git",
-                "reference": "f3adc98c1061875dd2edcd45e5b04e63d0e29f8f"
+                "reference": "fc47f1015ec80927ff64ba9094dfe8b9d48fe9f2"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/stopwatch/zipball/f3adc98c1061875dd2edcd45e5b04e63d0e29f8f",
-                "reference": "f3adc98c1061875dd2edcd45e5b04e63d0e29f8f",
+                "url": "https://api.github.com/repos/symfony/stopwatch/zipball/fc47f1015ec80927ff64ba9094dfe8b9d48fe9f2",
+                "reference": "fc47f1015ec80927ff64ba9094dfe8b9d48fe9f2",
                 "shasum": ""
             },
             "require": {
                 "php": ">=8.1",
-                "symfony/service-contracts": "^1|^2|^3"
+                "symfony/service-contracts": "^2.5|^3"
             },
             "type": "library",
             "autoload": {
@@ -1943,7 +1928,7 @@
             "description": "Provides a way to profile code",
             "homepage": "https://symfony.com",
             "support": {
-                "source": "https://github.com/symfony/stopwatch/tree/v6.2.7"
+                "source": "https://github.com/symfony/stopwatch/tree/v6.3.0"
             },
             "funding": [
                 {
@@ -1959,20 +1944,20 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-02-14T08:44:56+00:00"
+            "time": "2023-02-16T10:14:28+00:00"
         },
         {
             "name": "symfony/string",
-            "version": "v6.2.8",
+            "version": "v6.3.0",
             "source": {
                 "type": "git",
                 "url": "https://github.com/symfony/string.git",
-                "reference": "193e83bbd6617d6b2151c37fff10fa7168ebddef"
+                "reference": "f2e190ee75ff0f5eced645ec0be5c66fac81f51f"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/symfony/string/zipball/193e83bbd6617d6b2151c37fff10fa7168ebddef",
-                "reference": "193e83bbd6617d6b2151c37fff10fa7168ebddef",
+                "url": "https://api.github.com/repos/symfony/string/zipball/f2e190ee75ff0f5eced645ec0be5c66fac81f51f",
+                "reference": "f2e190ee75ff0f5eced645ec0be5c66fac81f51f",
                 "shasum": ""
             },
             "require": {
@@ -1983,13 +1968,13 @@
                 "symfony/polyfill-mbstring": "~1.0"
             },
             "conflict": {
-                "symfony/translation-contracts": "<2.0"
+                "symfony/translation-contracts": "<2.5"
             },
             "require-dev": {
                 "symfony/error-handler": "^5.4|^6.0",
                 "symfony/http-client": "^5.4|^6.0",
                 "symfony/intl": "^6.2",
-                "symfony/translation-contracts": "^2.0|^3.0",
+                "symfony/translation-contracts": "^2.5|^3.0",
                 "symfony/var-exporter": "^5.4|^6.0"
             },
             "type": "library",
@@ -2029,7 +2014,7 @@
                 "utf8"
             ],
             "support": {
-                "source": "https://github.com/symfony/string/tree/v6.2.8"
+                "source": "https://github.com/symfony/string/tree/v6.3.0"
             },
             "funding": [
                 {
@@ -2045,7 +2030,7 @@
                     "type": "tidelift"
                 }
             ],
-            "time": "2023-03-20T16:06:02+00:00"
+            "time": "2023-03-21T21:06:29+00:00"
         }
     ],
     "packages-dev": [],
diff --git a/app/Handlers/Events/APIEventHandler.php b/app/Handlers/Events/APIEventHandler.php
index 9d73bde36a..3c6d9b44b9 100644
--- a/app/Handlers/Events/APIEventHandler.php
+++ b/app/Handlers/Events/APIEventHandler.php
@@ -23,6 +23,7 @@ declare(strict_types=1);
 
 namespace FireflyIII\Handlers\Events;
 
+use Exception;
 use FireflyIII\Exceptions\FireflyException;
 use FireflyIII\Notifications\User\NewAccessToken;
 use FireflyIII\Repositories\User\UserRepositoryInterface;
@@ -50,7 +51,21 @@ class APIEventHandler
         $user       = $repository->find((int)$event->userId);
 
         if (null !== $user) {
-            Notification::send($user, new NewAccessToken());
+            try {
+                Notification::send($user, new NewAccessToken());
+            } catch (Exception $e) {
+                $message = $e->getMessage();
+                if (str_contains($message, 'Bcc')) {
+                    Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                    return;
+                }
+                if (str_contains($message, 'RFC 2822')) {
+                    Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                    return;
+                }
+                Log::error($e->getMessage());
+                Log::error($e->getTraceAsString());
+            }
         }
     }
 }
diff --git a/app/Handlers/Events/AdminEventHandler.php b/app/Handlers/Events/AdminEventHandler.php
index 768ba63f11..35b8d9499e 100644
--- a/app/Handlers/Events/AdminEventHandler.php
+++ b/app/Handlers/Events/AdminEventHandler.php
@@ -23,6 +23,7 @@ declare(strict_types=1);
 
 namespace FireflyIII\Handlers\Events;
 
+use Exception;
 use FireflyIII\Events\Admin\InvitationCreated;
 use FireflyIII\Events\AdminRequestedTestMessage;
 use FireflyIII\Events\NewVersionAvailable;
@@ -31,6 +32,7 @@ use FireflyIII\Notifications\Admin\UserInvitation;
 use FireflyIII\Notifications\Admin\VersionCheckResult;
 use FireflyIII\Repositories\User\UserRepositoryInterface;
 use FireflyIII\Support\Facades\FireflyConfig;
+use Illuminate\Support\Facades\Log;
 use Illuminate\Support\Facades\Notification;
 
 /**
@@ -54,7 +56,21 @@ class AdminEventHandler
         $all        = $repository->all();
         foreach ($all as $user) {
             if ($repository->hasRole($user, 'owner')) {
-                Notification::send($user, new UserInvitation($event->invitee));
+                try {
+                    Notification::send($user, new UserInvitation($event->invitee));
+                } catch (Exception $e) {
+                    $message = $e->getMessage();
+                    if (str_contains($message, 'Bcc')) {
+                        Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                        return;
+                    }
+                    if (str_contains($message, 'RFC 2822')) {
+                        Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                        return;
+                    }
+                    Log::error($e->getMessage());
+                    Log::error($e->getTraceAsString());
+                }
             }
         }
     }
@@ -77,7 +93,21 @@ class AdminEventHandler
         $all        = $repository->all();
         foreach ($all as $user) {
             if ($repository->hasRole($user, 'owner')) {
-                Notification::send($user, new VersionCheckResult($event->message));
+                try {
+                    Notification::send($user, new VersionCheckResult($event->message));
+                } catch (Exception $e) {
+                    $message = $e->getMessage();
+                    if (str_contains($message, 'Bcc')) {
+                        Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                        return;
+                    }
+                    if (str_contains($message, 'RFC 2822')) {
+                        Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                        return;
+                    }
+                    Log::error($e->getMessage());
+                    Log::error($e->getTraceAsString());
+                }
             }
         }
     }
@@ -97,7 +127,20 @@ class AdminEventHandler
         if (!$repository->hasRole($event->user, 'owner')) {
             return;
         }
-
-        Notification::send($event->user, new TestNotification($event->user->email));
+        try {
+            Notification::send($event->user, new TestNotification($event->user->email));
+        } catch (Exception $e) {
+            $message = $e->getMessage();
+            if (str_contains($message, 'Bcc')) {
+                Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                return;
+            }
+            if (str_contains($message, 'RFC 2822')) {
+                Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                return;
+            }
+            Log::error($e->getMessage());
+            Log::error($e->getTraceAsString());
+        }
     }
 }
diff --git a/app/Handlers/Events/AutomationHandler.php b/app/Handlers/Events/AutomationHandler.php
index f990032395..149dabbd85 100644
--- a/app/Handlers/Events/AutomationHandler.php
+++ b/app/Handlers/Events/AutomationHandler.php
@@ -23,6 +23,7 @@ declare(strict_types=1);
 
 namespace FireflyIII\Handlers\Events;
 
+use Exception;
 use FireflyIII\Events\RequestedReportOnJournals;
 use FireflyIII\Exceptions\FireflyException;
 use FireflyIII\Models\TransactionGroup;
@@ -66,7 +67,20 @@ class AutomationHandler
         foreach ($event->groups as $group) {
             $groups[] = $transformer->transformObject($group);
         }
-
-        Notification::send($user, new TransactionCreation($groups));
+        try {
+            Notification::send($user, new TransactionCreation($groups));
+        } catch (Exception $e) {
+            $message = $e->getMessage();
+            if (str_contains($message, 'Bcc')) {
+                Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                return;
+            }
+            if (str_contains($message, 'RFC 2822')) {
+                Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                return;
+            }
+            Log::error($e->getMessage());
+            Log::error($e->getTraceAsString());
+        }
     }
 }
diff --git a/app/Handlers/Events/BillEventHandler.php b/app/Handlers/Events/BillEventHandler.php
index 006f4af9d4..5ef5ff6541 100644
--- a/app/Handlers/Events/BillEventHandler.php
+++ b/app/Handlers/Events/BillEventHandler.php
@@ -24,6 +24,7 @@ declare(strict_types=1);
 
 namespace FireflyIII\Handlers\Events;
 
+use Exception;
 use FireflyIII\Events\WarnUserAboutBill;
 use FireflyIII\Notifications\User\BillReminder;
 use FireflyIII\Support\Facades\Preferences;
@@ -49,7 +50,21 @@ class BillEventHandler
 
         if (true === $preference) {
             Log::debug('Bill reminder is true!');
-            Notification::send($bill->user, new BillReminder($bill, $event->field, $event->diff));
+            try {
+                Notification::send($bill->user, new BillReminder($bill, $event->field, $event->diff));
+            } catch (Exception $e) {
+                $message = $e->getMessage();
+                if (str_contains($message, 'Bcc')) {
+                    Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                    return;
+                }
+                if (str_contains($message, 'RFC 2822')) {
+                    Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                    return;
+                }
+                Log::error($e->getMessage());
+                Log::error($e->getTraceAsString());
+            }
         }
         if (false === $preference) {
             Log::debug('User has disabled bill reminders.');
diff --git a/app/Handlers/Events/UserEventHandler.php b/app/Handlers/Events/UserEventHandler.php
index 1b5d6b2474..83af75e4dd 100644
--- a/app/Handlers/Events/UserEventHandler.php
+++ b/app/Handlers/Events/UserEventHandler.php
@@ -201,7 +201,21 @@ class UserEventHandler
         /** @var array $entry */
         foreach ($list as $index => $entry) {
             if (false === $entry['notified']) {
-                Notification::send($user, new UserLogin($ipAddress));
+                try {
+                    Notification::send($user, new UserLogin($ipAddress));
+                } catch (Exception $e) {
+                    $message = $e->getMessage();
+                    if (str_contains($message, 'Bcc')) {
+                        Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                        return;
+                    }
+                    if (str_contains($message, 'RFC 2822')) {
+                        Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                        return;
+                    }
+                    Log::error($e->getMessage());
+                    Log::error($e->getTraceAsString());
+                }
             }
             $list[$index]['notified'] = true;
         }
@@ -221,7 +235,21 @@ class UserEventHandler
             $all        = $repository->all();
             foreach ($all as $user) {
                 if ($repository->hasRole($user, 'owner')) {
-                    Notification::send($user, new AdminRegistrationNotification($event->user));
+                    try {
+                        Notification::send($user, new AdminRegistrationNotification($event->user));
+                    } catch (Exception $e) {
+                        $message = $e->getMessage();
+                        if (str_contains($message, 'Bcc')) {
+                            Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                            return;
+                        }
+                        if (str_contains($message, 'RFC 2822')) {
+                            Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                            return;
+                        }
+                        Log::error($e->getMessage());
+                        Log::error($e->getTraceAsString());
+                    }
                 }
             }
         }
@@ -281,7 +309,21 @@ class UserEventHandler
      */
     public function sendNewPassword(RequestedNewPassword $event): void
     {
-        Notification::send($event->user, new UserNewPassword(route('password.reset', [$event->token])));
+        try {
+            Notification::send($event->user, new UserNewPassword(route('password.reset', [$event->token])));
+        } catch (Exception $e) {
+            $message = $e->getMessage();
+            if (str_contains($message, 'Bcc')) {
+                Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                return;
+            }
+            if (str_contains($message, 'RFC 2822')) {
+                Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                return;
+            }
+            Log::error($e->getMessage());
+            Log::error($e->getTraceAsString());
+        }
     }
 
     /**
@@ -313,7 +355,21 @@ class UserEventHandler
     {
         $sendMail = FireflyConfig::get('notification_user_new_reg', true)->data;
         if ($sendMail) {
-            Notification::send($event->user, new UserRegistrationNotification());
+            try {
+                Notification::send($event->user, new UserRegistrationNotification());
+            } catch (Exception $e) {
+                $message = $e->getMessage();
+                if (str_contains($message, 'Bcc')) {
+                    Log::warning('[Bcc] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                    return;
+                }
+                if (str_contains($message, 'RFC 2822')) {
+                    Log::warning('[RFC] Could not send notification. Please validate your email settings, use the .env.example file as a guide.');
+                    return;
+                }
+                Log::error($e->getMessage());
+                Log::error($e->getTraceAsString());
+            }
         }
     }
 
diff --git a/app/Jobs/MailError.php b/app/Jobs/MailError.php
index 777601b3b6..ef17690a12 100644
--- a/app/Jobs/MailError.php
+++ b/app/Jobs/MailError.php
@@ -31,6 +31,7 @@ use Illuminate\Queue\InteractsWithQueue;
 use Illuminate\Queue\SerializesModels;
 use Illuminate\Support\Facades\Log;
 use Mail;
+use Symfony\Component\Mailer\Exception\TransportException;
 
 /**
  * Class MailError.
@@ -90,7 +91,7 @@ class MailError extends Job implements ShouldQueue
                         }
                     }
                 );
-            } catch (Exception $e) { // intentional generic exception
+            } catch (Exception|TransportException $e) { // intentional generic exception
                 $message = $e->getMessage();
                 if (str_contains($message, 'Bcc')) {
                     Log::warning('[Bcc] Could not email or log the error. Please validate your email settings, use the .env.example file as a guide.');