diff --git a/backend/src/ee/services/dynamic-secret/providers/models.ts b/backend/src/ee/services/dynamic-secret/providers/models.ts
index ae1bcfc25..c618a308b 100644
--- a/backend/src/ee/services/dynamic-secret/providers/models.ts
+++ b/backend/src/ee/services/dynamic-secret/providers/models.ts
@@ -165,6 +165,7 @@ export const DynamicSecretSqlDBSchema = z.object({
   revocationStatement: z.string().trim(),
   renewStatement: z.string().trim().optional(),
   ca: z.string().optional(),
+  sslEnabled: z.boolean().optional(),
   gatewayId: z.string().nullable().optional()
 });
 
diff --git a/backend/src/ee/services/dynamic-secret/providers/sql-database.ts b/backend/src/ee/services/dynamic-secret/providers/sql-database.ts
index e68e41c6b..2b9636724 100644
--- a/backend/src/ee/services/dynamic-secret/providers/sql-database.ts
+++ b/backend/src/ee/services/dynamic-secret/providers/sql-database.ts
@@ -1,4 +1,5 @@
 import handlebars from "handlebars";
+import RE2 from "re2";
 import knex from "knex";
 import { z } from "zod";
 
@@ -150,12 +151,30 @@ export const SqlDatabaseProvider = ({ gatewayService }: TSqlDatabaseProviderDTO)
     return { ...providerInputs, hostIp };
   };
 
-  const $getClient = async (providerInputs: z.infer<typeof DynamicSecretSqlDBSchema> & { hostIp: string }) => {
+  const $getClient = async (
+    providerInputs: z.infer<typeof DynamicSecretSqlDBSchema> & { hostIp: string; originalHost: string }
+  ) => {
     const ssl = providerInputs.ca
       ? { rejectUnauthorized: false, ca: providerInputs.ca, servername: providerInputs.host }
       : undefined;
+
     const isMsSQLClient = providerInputs.client === SqlProviders.MsSQL;
 
+    /*
+      We route through the gateway by setting connection.host = "localhost".
+      Azure SQL identifies the logical server from the TDS login name when the host
+      isn’t the Azure FQDN. Therefore, when using the gateway, ensure username is
+      "user@<azure-server-name>" so Azure opens the correct logical server.
+      Direct connections to the Azure FQDN usually don’t require this suffix.
+    */
+    const isAzureSql = isMsSQLClient && new RE2(/\.database\.windows\.net$/i).test(providerInputs.originalHost);
+    const azureServerLabel =
+      isAzureSql && providerInputs.gatewayId ? providerInputs.originalHost?.split(".")[0] : undefined;
+    const effectiveUser =
+      isAzureSql && !providerInputs.username.includes("@") && azureServerLabel
+        ? `${providerInputs.username}@${azureServerLabel}`
+        : providerInputs.username;
+
     const db = knex({
       client: providerInputs.client,
       connection: {
@@ -165,7 +184,7 @@ export const SqlDatabaseProvider = ({ gatewayService }: TSqlDatabaseProviderDTO)
           providerInputs.client === SqlProviders.Postgres && !providerInputs.gatewayId
             ? providerInputs.hostIp
             : providerInputs.host,
-        user: providerInputs.username,
+        user: effectiveUser,
         password: providerInputs.password,
         ssl,
         // @ts-expect-error this is because of knexjs type signature issue. This is directly passed to driver
@@ -173,6 +192,7 @@ export const SqlDatabaseProvider = ({ gatewayService }: TSqlDatabaseProviderDTO)
         // https://github.com/tediousjs/tedious/blob/ebb023ed90969a7ec0e4b036533ad52739d921f7/test/config.ci.ts#L19
         options: isMsSQLClient
           ? {
+              ...(providerInputs.sslEnabled !== undefined ? { encrypt: providerInputs.sslEnabled } : {}),
               trustServerCertificate: !providerInputs.ca,
               cryptoCredentialsDetails: providerInputs.ca ? { ca: providerInputs.ca } : {}
             }
@@ -215,7 +235,13 @@ export const SqlDatabaseProvider = ({ gatewayService }: TSqlDatabaseProviderDTO)
     const providerInputs = await validateProviderInputs(inputs);
     let isConnected = false;
     const gatewayCallback = async (host = providerInputs.host, port = providerInputs.port) => {
-      const db = await $getClient({ ...providerInputs, port, host, hostIp: providerInputs.hostIp });
+      const db = await $getClient({
+        ...providerInputs,
+        port,
+        host,
+        hostIp: providerInputs.hostIp,
+        originalHost: providerInputs.host
+      });
       // oracle needs from keyword
       const testStatement = providerInputs.client === SqlProviders.Oracle ? "SELECT 1 FROM DUAL" : "SELECT 1";
 
@@ -256,7 +282,12 @@ export const SqlDatabaseProvider = ({ gatewayService }: TSqlDatabaseProviderDTO)
 
     const password = generatePassword(providerInputs.client, providerInputs.passwordRequirements);
     const gatewayCallback = async (host = providerInputs.host, port = providerInputs.port) => {
-      const db = await $getClient({ ...providerInputs, port, host });
+      const db = await $getClient({
+        ...providerInputs,
+        port,
+        host,
+        originalHost: providerInputs.host
+      });
       try {
         const expiration = new Date(expireAt).toISOString();
 
@@ -299,7 +330,12 @@ export const SqlDatabaseProvider = ({ gatewayService }: TSqlDatabaseProviderDTO)
     const username = entityId;
     const { database } = providerInputs;
     const gatewayCallback = async (host = providerInputs.host, port = providerInputs.port) => {
-      const db = await $getClient({ ...providerInputs, port, host });
+      const db = await $getClient({
+        ...providerInputs,
+        port,
+        host,
+        originalHost: providerInputs.host
+      });
       try {
         const revokeStatement = handlebars.compile(providerInputs.revocationStatement)({ username, database });
         const queries = revokeStatement.toString().split(";").filter(Boolean);
@@ -334,7 +370,12 @@ export const SqlDatabaseProvider = ({ gatewayService }: TSqlDatabaseProviderDTO)
     if (!providerInputs.renewStatement) return { entityId };
 
     const gatewayCallback = async (host = providerInputs.host, port = providerInputs.port) => {
-      const db = await $getClient({ ...providerInputs, port, host });
+      const db = await $getClient({
+        ...providerInputs,
+        port,
+        host,
+        originalHost: providerInputs.host
+      });
       const expiration = new Date(expireAt).toISOString();
       const { database } = providerInputs;
 
diff --git a/frontend/src/pages/secret-manager/SecretDashboardPage/components/ActionBar/CreateDynamicSecretForm/SqlDatabaseInputForm.tsx b/frontend/src/pages/secret-manager/SecretDashboardPage/components/ActionBar/CreateDynamicSecretForm/SqlDatabaseInputForm.tsx
index 8bedbbaeb..050a51754 100644
--- a/frontend/src/pages/secret-manager/SecretDashboardPage/components/ActionBar/CreateDynamicSecretForm/SqlDatabaseInputForm.tsx
+++ b/frontend/src/pages/secret-manager/SecretDashboardPage/components/ActionBar/CreateDynamicSecretForm/SqlDatabaseInputForm.tsx
@@ -19,6 +19,7 @@ import {
   SecretInput,
   Select,
   SelectItem,
+  Switch,
   TextArea,
   Tooltip
 } from "@app/components/v2";
@@ -66,6 +67,7 @@ const formSchema = z.object({
     creationStatement: z.string().min(1),
     revocationStatement: z.string().min(1),
     renewStatement: z.string().optional(),
+    sslEnabled: z.boolean().optional(),
     ca: z.string().optional(),
     gatewayId: z.string().optional()
   }),
@@ -200,6 +202,7 @@ export const SqlDatabaseInputForm = ({
 
   const createDynamicSecret = useCreateDynamicSecret();
   const { data: gateways, isPending: isGatewaysLoading } = useQuery(gatewaysQueryKeys.list());
+  const selectedClient = watch("provider.client");
 
   const handleCreateDynamicSecret = async ({
     name,
@@ -458,13 +461,34 @@ export const SqlDatabaseInputForm = ({
                 />
               </div>
               <div>
+                {selectedClient === SqlProviders.MsSQL && (
+                  <div className="mb-2 mt-2">
+                    <Controller
+                      control={control}
+                      name="provider.sslEnabled"
+                      render={({ field: { value, onChange }, fieldState: { error } }) => (
+                        <FormControl isError={Boolean(error?.message)} errorText={error?.message}>
+                          <Switch
+                            className="bg-mineshaft-400/50 shadow-inner data-[state=checked]:bg-green/80"
+                            id="sql-ds-ssl-enabled"
+                            thumbClassName="bg-mineshaft-800"
+                            isChecked={value}
+                            onCheckedChange={onChange}
+                          >
+                            Encrypt Connection (SSL)
+                          </Switch>
+                        </FormControl>
+                      )}
+                    />
+                  </div>
+                )}
                 <Controller
                   control={control}
                   name="provider.ca"
                   render={({ field, fieldState: { error } }) => (
                     <FormControl
                       isOptional
-                      label="CA(SSL)"
+                      label="CA (SSL)"
                       isError={Boolean(error?.message)}
                       errorText={error?.message}
                     >
diff --git a/frontend/src/pages/secret-manager/SecretDashboardPage/components/DynamicSecretListView/EditDynamicSecretForm/EditDynamicSecretSqlProviderForm.tsx b/frontend/src/pages/secret-manager/SecretDashboardPage/components/DynamicSecretListView/EditDynamicSecretForm/EditDynamicSecretSqlProviderForm.tsx
index 2cbad1e19..1eda17bc8 100644
--- a/frontend/src/pages/secret-manager/SecretDashboardPage/components/DynamicSecretListView/EditDynamicSecretForm/EditDynamicSecretSqlProviderForm.tsx
+++ b/frontend/src/pages/secret-manager/SecretDashboardPage/components/DynamicSecretListView/EditDynamicSecretForm/EditDynamicSecretSqlProviderForm.tsx
@@ -18,6 +18,7 @@ import {
   SecretInput,
   Select,
   SelectItem,
+  Switch,
   TextArea,
   Tooltip
 } from "@app/components/v2";
@@ -63,6 +64,7 @@ const formSchema = z.object({
       creationStatement: z.string().min(1),
       revocationStatement: z.string().min(1),
       renewStatement: z.string().optional(),
+      sslEnabled: z.boolean().optional(),
       ca: z.string().optional(),
       gatewayId: z.string().optional().nullable()
     })
@@ -151,6 +153,7 @@ export const EditDynamicSecretSqlProviderForm = ({
   });
 
   const { data: gateways, isPending: isGatewaysLoading } = useQuery(gatewaysQueryKeys.list());
+  const selectedClient = watch("inputs.client");
 
   const updateDynamicSecret = useUpdateDynamicSecret();
   const selectedGatewayId = watch("inputs.gatewayId");
@@ -407,13 +410,34 @@ export const EditDynamicSecretSqlProviderForm = ({
               />
             </div>
             <div>
+              {selectedClient === SqlProviders.MsSQL && (
+                <div className="mb-2 mt-2">
+                  <Controller
+                    control={control}
+                    name="inputs.sslEnabled"
+                    render={({ field: { value, onChange }, fieldState: { error } }) => (
+                      <FormControl isError={Boolean(error?.message)} errorText={error?.message}>
+                        <Switch
+                          className="bg-mineshaft-400/50 shadow-inner data-[state=checked]:bg-green/80"
+                          id="sql-ds-ssl-enabled"
+                          thumbClassName="bg-mineshaft-800"
+                          isChecked={Boolean(value)}
+                          onCheckedChange={onChange}
+                        >
+                          Encrypt Connection (SSL)
+                        </Switch>
+                      </FormControl>
+                    )}
+                  />
+                </div>
+              )}
               <Controller
                 control={control}
                 name="inputs.ca"
                 render={({ field, fieldState: { error } }) => (
                   <FormControl
                     isOptional
-                    label="CA(SSL)"
+                    label="CA (SSL)"
                     isError={Boolean(error?.message)}
                     errorText={error?.message}
                   >