diff --git a/plugins/storage/server/utils.ts b/plugins/storage/server/utils.ts
index c3c88fba5..13520b9d1 100644
--- a/plugins/storage/server/utils.ts
+++ b/plugins/storage/server/utils.ts
@@ -12,7 +12,7 @@ export const createRootDirForLocalStorage = () => {
       }
     } catch (err) {
       Logger.fatal(
-        "Couldn't create root dir for local storage of attachments",
+        `Failed to create directory for local file storage at ${env.FILE_STORAGE_LOCAL_ROOT_DIR}`,
         err
       );
     }
diff --git a/server/index.ts b/server/index.ts
index 781410bb5..c4d34acfe 100644
--- a/server/index.ts
+++ b/server/index.ts
@@ -23,7 +23,7 @@ import { checkEnv, checkPendingMigrations } from "./utils/startup";
 import { checkUpdates } from "./utils/updates";
 import onerror from "./onerror";
 import ShutdownHelper, { ShutdownOrder } from "./utils/ShutdownHelper";
-import { sequelize } from "./storage/database";
+import { checkConnection, sequelize } from "./storage/database";
 import RedisAdapter from "./storage/redis";
 import Metrics from "./logging/Metrics";
 
@@ -50,6 +50,7 @@ if (serviceNames.includes("collaboration")) {
 
 // This function will only be called once in the original process
 async function master() {
+  await checkConnection();
   await checkEnv();
   await checkPendingMigrations();
 
diff --git a/server/storage/database.ts b/server/storage/database.ts
index b0e99eed0..3e1e98f88 100644
--- a/server/storage/database.ts
+++ b/server/storage/database.ts
@@ -5,6 +5,7 @@ import env from "@server/env";
 import Logger from "../logging/Logger";
 import * as models from "../models";
 
+const isDevelopment = env.ENVIRONMENT === "development";
 const isProduction = env.ENVIRONMENT === "production";
 const isSSLDisabled = env.PGSSLMODE === "disable";
 const poolMax = env.DATABASE_CONNECTION_POOL_MAX ?? 5;
@@ -18,6 +19,7 @@ export const sequelize = new Sequelize(url, {
   logging: (msg) =>
     process.env.DEBUG?.includes("database") && Logger.debug("database", msg),
   typeValidation: true,
+  logQueryParameters: isDevelopment,
   dialectOptions: {
     ssl:
       isProduction && !isSSLDisabled
@@ -36,6 +38,25 @@ export const sequelize = new Sequelize(url, {
   },
 });
 
+/**
+ * This function is used to test the database connection on startup. It will
+ * throw a descriptive error if the connection fails.
+ */
+export const checkConnection = async () => {
+  try {
+    await sequelize.authenticate();
+  } catch (error) {
+    if (error.message.includes("does not support SSL")) {
+      Logger.fatal(
+        "The database does not support SSL connections. Set the `PGSSLMODE` environment variable to `disable` or enable SSL on your database server.",
+        error
+      );
+    } else {
+      Logger.fatal("Failed to connect to database", error);
+    }
+  }
+};
+
 export const migrations = new Umzug({
   migrations: {
     glob: ["migrations/*.js", { cwd: path.resolve("server") }],