diff --git a/backend/e2e-test/mocks/smtp.ts b/backend/e2e-test/mocks/smtp.ts
index 9f83f7134a..4ba42e8389 100644
--- a/backend/e2e-test/mocks/smtp.ts
+++ b/backend/e2e-test/mocks/smtp.ts
@@ -5,6 +5,9 @@ export const mockSmtpServer = (): TSmtpService => {
   return {
     sendMail: async (data) => {
       storage.push(data);
+    },
+    verify: async () => {
+      return true;
     }
   };
 };
diff --git a/backend/src/ee/services/oidc/oidc-config-service.ts b/backend/src/ee/services/oidc/oidc-config-service.ts
index 17c1ddaaf2..45a58bd1ea 100644
--- a/backend/src/ee/services/oidc/oidc-config-service.ts
+++ b/backend/src/ee/services/oidc/oidc-config-service.ts
@@ -17,7 +17,7 @@ import {
   infisicalSymmetricDecrypt,
   infisicalSymmetricEncypt
 } from "@app/lib/crypto/encryption";
-import { BadRequestError, ForbiddenRequestError, NotFoundError } from "@app/lib/errors";
+import { BadRequestError, ForbiddenRequestError, NotFoundError, OidcAuthError } from "@app/lib/errors";
 import { AuthMethod, AuthTokenType } from "@app/services/auth/auth-type";
 import { TAuthTokenServiceFactory } from "@app/services/auth-token/auth-token-service";
 import { TokenType } from "@app/services/auth-token/auth-token-types";
@@ -56,7 +56,7 @@ type TOidcConfigServiceFactoryDep = {
   orgBotDAL: Pick<TOrgBotDALFactory, "findOne" | "create" | "transaction">;
   licenseService: Pick<TLicenseServiceFactory, "getPlan" | "updateSubscriptionOrgMemberCount">;
   tokenService: Pick<TAuthTokenServiceFactory, "createTokenForUser">;
-  smtpService: Pick<TSmtpService, "sendMail">;
+  smtpService: Pick<TSmtpService, "sendMail" | "verify">;
   permissionService: Pick<TPermissionServiceFactory, "getOrgPermission">;
   oidcConfigDAL: Pick<TOidcConfigDALFactory, "findOne" | "update" | "create">;
 };
@@ -223,6 +223,7 @@ export const oidcConfigServiceFactory = ({
         let newUser: TUsers | undefined;
 
         if (serverCfg.trustOidcEmails) {
+          // we prioritize getting the most complete user to create the new alias under
           newUser = await userDAL.findOne(
             {
               email,
@@ -230,6 +231,23 @@ export const oidcConfigServiceFactory = ({
             },
             tx
           );
+
+          if (!newUser) {
+            // this fetches user entries created via invites
+            newUser = await userDAL.findOne(
+              {
+                username: email
+              },
+              tx
+            );
+
+            if (newUser && !newUser.isEmailVerified) {
+              // we automatically mark it as email-verified because we've configured trust for OIDC emails
+              newUser = await userDAL.updateById(newUser.id, {
+                isEmailVerified: true
+              });
+            }
+          }
         }
 
         if (!newUser) {
@@ -332,14 +350,20 @@ export const oidcConfigServiceFactory = ({
         userId: user.id
       });
 
-      await smtpService.sendMail({
-        template: SmtpTemplates.EmailVerification,
-        subjectLine: "Infisical confirmation code",
-        recipients: [user.email],
-        substitutions: {
-          code: token
-        }
-      });
+      await smtpService
+        .sendMail({
+          template: SmtpTemplates.EmailVerification,
+          subjectLine: "Infisical confirmation code",
+          recipients: [user.email],
+          substitutions: {
+            code: token
+          }
+        })
+        .catch((err: Error) => {
+          throw new OidcAuthError({
+            message: `Error sending email confirmation code for user registration - contact the Infisical instance admin. ${err.message}`
+          });
+        });
     }
 
     return { isUserCompleted, providerAuthToken };
@@ -395,6 +419,18 @@ export const oidcConfigServiceFactory = ({
         message: `Organization bot for organization with ID '${org.id}' not found`,
         name: "OrgBotNotFound"
       });
+
+    const serverCfg = await getServerCfg();
+    if (isActive && !serverCfg.trustOidcEmails) {
+      const isSmtpConnected = await smtpService.verify();
+      if (!isSmtpConnected) {
+        throw new BadRequestError({
+          message:
+            "Cannot enable OIDC when there are issues with the instance's SMTP configuration. Bypass this by turning on trust for OIDC emails in the server admin console."
+        });
+      }
+    }
+
     const key = infisicalSymmetricDecrypt({
       ciphertext: orgBot.encryptedSymmetricKey,
       iv: orgBot.symmetricKeyIV,
diff --git a/backend/src/lib/errors/index.ts b/backend/src/lib/errors/index.ts
index 0818cfe7d9..cc1c1d66b4 100644
--- a/backend/src/lib/errors/index.ts
+++ b/backend/src/lib/errors/index.ts
@@ -133,3 +133,15 @@ export class ScimRequestError extends Error {
     this.status = status;
   }
 }
+
+export class OidcAuthError extends Error {
+  name: string;
+
+  error: unknown;
+
+  constructor({ name, error, message }: { message?: string; name?: string; error?: unknown }) {
+    super(message || "Something went wrong");
+    this.name = name || "OidcAuthError";
+    this.error = error;
+  }
+}
diff --git a/backend/src/server/boot-strap-check.ts b/backend/src/server/boot-strap-check.ts
index ceaef59e7f..7db2a71e82 100644
--- a/backend/src/server/boot-strap-check.ts
+++ b/backend/src/server/boot-strap-check.ts
@@ -46,10 +46,10 @@ export const bootstrapCheck = async ({ db }: BootstrapOpt) => {
   await createTransport(smtpCfg)
     .verify()
     .then(async () => {
-      console.info("SMTP successfully connected");
+      console.info(`SMTP - Verified connection to ${appCfg.SMTP_HOST}:${appCfg.SMTP_PORT}`);
     })
-    .catch((err) => {
-      console.error(`SMTP - Failed to connect to ${appCfg.SMTP_HOST}:${appCfg.SMTP_PORT}`);
+    .catch((err: Error) => {
+      console.error(`SMTP - Failed to connect to ${appCfg.SMTP_HOST}:${appCfg.SMTP_PORT} - ${err.message}`);
       logger.error(err);
     });
 
diff --git a/backend/src/server/plugins/error-handler.ts b/backend/src/server/plugins/error-handler.ts
index 007902a176..c08b2fe4c7 100644
--- a/backend/src/server/plugins/error-handler.ts
+++ b/backend/src/server/plugins/error-handler.ts
@@ -10,6 +10,7 @@ import {
   GatewayTimeoutError,
   InternalServerError,
   NotFoundError,
+  OidcAuthError,
   RateLimitError,
   ScimRequestError,
   UnauthorizedError
@@ -83,7 +84,10 @@ export const fastifyErrHandler = fastifyPlugin(async (server: FastifyZodProvider
         status: error.status,
         detail: error.detail
       });
-      // Handle JWT errors and make them more human-readable for the end-user.
+    } else if (error instanceof OidcAuthError) {
+      void res
+        .status(HttpStatusCodes.InternalServerError)
+        .send({ statusCode: HttpStatusCodes.InternalServerError, message: error.message, error: error.name });
     } else if (error instanceof jwt.JsonWebTokenError) {
       const message = (() => {
         if (error.message === JWTErrors.JwtExpired) {
diff --git a/backend/src/services/smtp/smtp-service.ts b/backend/src/services/smtp/smtp-service.ts
index 1f38babb37..bdf2fe18c5 100644
--- a/backend/src/services/smtp/smtp-service.ts
+++ b/backend/src/services/smtp/smtp-service.ts
@@ -77,5 +77,21 @@ export const smtpServiceFactory = (cfg: TSmtpConfig) => {
     }
   };
 
-  return { sendMail };
+  const verify = async () => {
+    const isConnected = smtp
+      .verify()
+      .then(async () => {
+        logger.info("SMTP connected");
+        return true;
+      })
+      .catch((err: Error) => {
+        logger.error("SMTP error");
+        logger.error(err);
+        return false;
+      });
+
+    return isConnected;
+  };
+
+  return { sendMail, verify };
 };