diff --git a/apps/desktop/src/components/editor/QueryEditor.vue b/apps/desktop/src/components/editor/QueryEditor.vue
index 5739d619e..1ad9f4f23 100644
--- a/apps/desktop/src/components/editor/QueryEditor.vue
+++ b/apps/desktop/src/components/editor/QueryEditor.vue
@@ -15,6 +15,7 @@ import { buildExecutionCandidates, hasMultipleExecutionTargets, supportsExecutio
 import { executableStatementRangeAtCursor, executableStatementRangeCacheForDoc, executableStatementRangeStartingAt as executableStatementRangeStartingAtLine, type ExecutableStatementRangeCache } from "@/lib/sql/executableStatementRangeCache";
 import { currentStatementFrameRangeTo, visualSqlColumnsWithInlineHints } from "@/lib/sql/currentStatementFrame";
 import { expandToSqlStatementWindow, parseInsertValueHints } from "@/lib/sql/insertValueHints";
+import { insertValueHintColumnNames } from "@/lib/sql/insertValueHintColumns";
 import { formatSqlText, type SqlFormatDialect } from "@/lib/sql/sqlFormatter";
 import { blankLineDeletionChanges, replaceSelectedEditorText } from "@/lib/editor/queryEditorTextEdits";
 import { buildSqlInConditionFromPasteSource, insertTextForSqlInCondition } from "@/lib/sql/sqlInListPaste";
@@ -67,6 +68,7 @@ import { sqlSemanticTableNameSpansForSyntaxTree } from "@/lib/editor/codemirrorS
 import { startsQueryEditorRectangularSelection } from "@/lib/editor/queryEditorPointerSelection";
 import type { StatementExecutionMarker } from "@/lib/tabs/tabPresentation";
 import { isSchemaAware, isSingleDatabase, supportsSqlInListPaste } from "@/lib/database/databaseFeatureSupport";
+import { metadataSchemaForConnection } from "@/lib/database/jdbcDialect";
 import { usesLocalOnlyEditorCompletionMetadata, usesOnDemandOnlyEditorColumnMetadata } from "@/lib/metadata/completionMetadataPolicy";
 import { queryContextObjectActions, queryContextObjectRoute, queryTableCandidateAtSqlPosition, resolveQueryContextCandidateDatabase, resolveQueryContextObjectTarget, type QueryContextObjectAction } from "@/lib/sql/queryCursorTableTarget";
 import * as api from "@/lib/backend/api";
@@ -329,6 +331,7 @@ let cachedTables: SqlCompletionTable[] = [];
 let cachedCompletionObjects: SqlCompletionObject[] = [];
 // Persistent column cache keyed by "schema.table" or "table"
 const cachedColumnsByTable = new Map<string, SqlCompletionColumn[]>();
+const cachedInsertValueHintColumnsByTable = new Map<string, string[]>();
 const cachedForeignKeysByTable = new Map<string, SqlCompletionForeignKey[]>();
 const loadedColumnsByTable = new Set<string>();
 
@@ -1332,6 +1335,7 @@ function insertHintMetadataTarget(table: { name: string; schema?: string | null;
 
 function getInsertValueHintTableColumns(table: string, schema?: string, database?: string): string[] | undefined {
   const cacheKey = insertHintCacheKey({ name: table, schema, database });
+  if (props.databaseType === "sqlserver") return cachedInsertValueHintColumnsByTable.get(cacheKey);
   const cached = cachedColumnsByTable.get(cacheKey);
   if (!cached) return undefined;
   return cached.map((column) => column.name);
@@ -1341,14 +1345,25 @@ function requestInsertValueHintTableColumns(table: string, schema?: string, data
   if (!props.connectionId || props.database == null) return;
   if (props.databaseType === "redis" || props.databaseType === "mongodb" || props.databaseType === "elasticsearch") return;
   const cacheKey = insertHintCacheKey({ name: table, schema, database });
-  if (cachedColumnsByTable.has(cacheKey) || pendingInsertValueHintColumnLoads.has(cacheKey)) return;
+  const hasCachedColumns = props.databaseType === "sqlserver" ? cachedInsertValueHintColumnsByTable.has(cacheKey) : cachedColumnsByTable.has(cacheKey);
+  if (hasCachedColumns || pendingInsertValueHintColumnLoads.has(cacheKey)) return;
   const target = insertHintMetadataTarget({ name: table, schema, database });
   if (!target) return;
   pendingInsertValueHintColumnLoads.add(cacheKey);
-  void connectionStore
-    .listCompletionColumns(props.connectionId, target.database, table, target.schema)
-    .then((columns) => {
-      cachedColumnsByTable.set(cacheKey, columns);
+  const connectionId = props.connectionId;
+  const databaseType = props.databaseType;
+  const loadColumns = async () => {
+    if (databaseType === "sqlserver") {
+      const querySchema = metadataSchemaForConnection(connectionStore.getConfig(connectionId), target.database, target.schema);
+      const columns = await api.getSqlServerColumnMetadata(connectionId, target.database, querySchema, table);
+      cachedInsertValueHintColumnsByTable.set(cacheKey, insertValueHintColumnNames(databaseType, columns));
+      return;
+    }
+    const columns = await connectionStore.listCompletionColumns(connectionId, target.database, table, target.schema);
+    cachedColumnsByTable.set(cacheKey, columns);
+  };
+  void loadColumns()
+    .then(() => {
       loadedColumnsByTable.add(cacheKey.toLowerCase());
       if (view.value) requestInsertValueHintsRefresh(view.value);
     })
@@ -2923,6 +2938,7 @@ function refreshCompletionCache() {
   cachedTables = [];
   cachedCompletionObjects = [];
   cachedColumnsByTable.clear();
+  cachedInsertValueHintColumnsByTable.clear();
   loadedColumnsByTable.clear();
   cachedForeignKeysByTable.clear();
 }
diff --git a/apps/desktop/src/lib/backend/api.ts b/apps/desktop/src/lib/backend/api.ts
index 87f699bee..14737842e 100644
--- a/apps/desktop/src/lib/backend/api.ts
+++ b/apps/desktop/src/lib/backend/api.ts
@@ -151,6 +151,7 @@ export const listCompletionObjects = forward("listCompletionObjects");
 export const completionAssistantSearch = forward("completionAssistantSearch");
 export const getObjectSource = forward("getObjectSource");
 export const getColumns = forward("getColumns");
+export const getSqlServerColumnMetadata = forward("getSqlServerColumnMetadata");
 export const listDataTypes = forward("listDataTypes");
 export const listIndexes = forward("listIndexes");
 export const listForeignKeys = forward("listForeignKeys");
diff --git a/apps/desktop/src/lib/backend/http.ts b/apps/desktop/src/lib/backend/http.ts
index 46fa4af69..fef1df75c 100644
--- a/apps/desktop/src/lib/backend/http.ts
+++ b/apps/desktop/src/lib/backend/http.ts
@@ -14,6 +14,7 @@ import type {
   ObjectSource,
   ObjectSourceKind,
   ColumnInfo,
+  SqlServerColumnMetadata,
   IndexInfo,
   ForeignKeyInfo,
   TriggerInfo,
@@ -640,6 +641,10 @@ export async function getColumns(connectionId: string, database: string, schema:
   return get(`/api/schema/columns?${qs({ connection_id: connectionId, database, schema, table, catalog })}`);
 }
 
+export async function getSqlServerColumnMetadata(connectionId: string, database: string, schema: string, table: string): Promise<SqlServerColumnMetadata[]> {
+  return get(`/api/schema/sqlserver/column-metadata?${qs({ connection_id: connectionId, database, schema, table })}`);
+}
+
 export async function listDataTypes(connectionId: string, database: string): Promise<string[]> {
   return get(`/api/schema/data-types?${qs({ connection_id: connectionId, database })}`);
 }
diff --git a/apps/desktop/src/lib/backend/tauri.ts b/apps/desktop/src/lib/backend/tauri.ts
index 18d70c7b6..036a3f278 100644
--- a/apps/desktop/src/lib/backend/tauri.ts
+++ b/apps/desktop/src/lib/backend/tauri.ts
@@ -17,6 +17,7 @@ import type {
   ObjectSource,
   ObjectSourceKind,
   ColumnInfo,
+  SqlServerColumnMetadata,
   IndexInfo,
   ForeignKeyInfo,
   TriggerInfo,
@@ -789,6 +790,10 @@ export async function getColumns(connectionId: string, database: string, schema:
   return invoke("get_columns", { connectionId, database, schema, table, catalog });
 }
 
+export async function getSqlServerColumnMetadata(connectionId: string, database: string, schema: string, table: string): Promise<SqlServerColumnMetadata[]> {
+  return invoke("get_sqlserver_column_metadata", { connectionId, database, schema, table });
+}
+
 export async function listDataTypes(connectionId: string, database: string): Promise<string[]> {
   return invoke("list_data_types", { connectionId, database });
 }
diff --git a/apps/desktop/src/lib/sql/insertValueHintColumns.ts b/apps/desktop/src/lib/sql/insertValueHintColumns.ts
new file mode 100644
index 000000000..db023fc39
--- /dev/null
+++ b/apps/desktop/src/lib/sql/insertValueHintColumns.ts
@@ -0,0 +1,14 @@
+import type { DatabaseType, SqlServerColumnMetadata } from "@/types/database";
+
+type InsertValueHintColumn = Pick<SqlServerColumnMetadata, "name"> & Partial<Pick<SqlServerColumnMetadata, "is_identity" | "is_computed" | "is_hidden" | "generated_always_type">>;
+
+export function insertValueHintColumnNames(databaseType: DatabaseType | undefined, columns: readonly InsertValueHintColumn[]): string[] {
+  return columns
+    .filter((column) => {
+      if (databaseType !== "sqlserver") return true;
+      // SQL Server reports computed and temporal period columns independently;
+      // check every structured flag so positional VALUES only maps writable columns.
+      return !column.is_identity && !column.is_computed && !column.is_hidden && (column.generated_always_type ?? 0) === 0;
+    })
+    .map((column) => column.name);
+}
diff --git a/apps/desktop/src/types/database.ts b/apps/desktop/src/types/database.ts
index 5ed7d752a..7e1ddd2af 100644
--- a/apps/desktop/src/types/database.ts
+++ b/apps/desktop/src/types/database.ts
@@ -425,6 +425,13 @@ export interface ColumnInfo {
   collation?: string | null;
 }
 
+export interface SqlServerColumnMetadata extends ColumnInfo {
+  is_identity: boolean;
+  is_computed: boolean;
+  is_hidden: boolean;
+  generated_always_type: number;
+}
+
 export interface IndexInfo {
   name: string;
   columns: string[];
diff --git a/crates/dbx-core/src/db/sqlserver.rs b/crates/dbx-core/src/db/sqlserver.rs
index 72fd98f15..9d57735a9 100644
--- a/crates/dbx-core/src/db/sqlserver.rs
+++ b/crates/dbx-core/src/db/sqlserver.rs
@@ -9,7 +9,7 @@ use std::future::Future;
 use std::panic::AssertUnwindSafe;
 use std::sync::{Arc as StdArc, Mutex as StdMutex};
 use std::time::{Duration, Instant};
-use tiberius::{AuthMethod, Client, ColumnData, ColumnType, Config, FromSql, QueryItem, QueryStream, SqlBrowser};
+use tiberius::{AuthMethod, Client, ColumnData, ColumnType, Config, FromSql, QueryItem, QueryStream, Row, SqlBrowser};
 use tokio::net::TcpStream;
 use tokio_util::compat::{Compat, TokioAsyncWriteCompatExt};
 use tokio_util::sync::CancellationToken;
@@ -34,6 +34,16 @@ const SQLSERVER_LEGACY_ENCRYPTION_FALLBACKS: [(&str, tiberius::EncryptionLevel);
     ("no-encryption compatibility fallback", SQLSERVER_UNSUPPORTED_ENCRYPTION_LEVEL),
 ];
 
+#[derive(Debug, Clone, serde::Serialize, serde::Deserialize)]
+pub struct SqlServerColumnMetadata {
+    #[serde(flatten)]
+    pub column: ColumnInfo,
+    pub is_identity: bool,
+    pub is_computed: bool,
+    pub is_hidden: bool,
+    pub generated_always_type: i32,
+}
+
 #[derive(Debug, PartialEq, Eq)]
 struct SqlServerEndpoint<'a> {
     host: &'a str,
@@ -1520,88 +1530,104 @@ pub async fn list_object_statistics(
 }
 
 pub async fn get_columns(client: &mut SqlServerClient, schema: &str, table: &str) -> Result<Vec<ColumnInfo>, String> {
+    Ok(get_column_metadata(client, schema, table).await?.into_iter().map(|metadata| metadata.column).collect())
+}
+
+pub async fn get_column_metadata(
+    client: &mut SqlServerClient,
+    schema: &str,
+    table: &str,
+) -> Result<Vec<SqlServerColumnMetadata>, String> {
     let sql = sqlserver_columns_sql(schema, table);
     let stream = client.query(&*sql, &[]).await.map_err(|e| e.to_string())?;
     let rows = stream.into_first_result().await.map_err(|e| e.to_string())?;
-    Ok(rows
-        .iter()
-        .map(|row| {
-            let base = row.get::<&str, _>(1).unwrap_or("").to_string();
-            let max_len = row
-                .try_get::<i32, _>(7)
-                .ok()
-                .flatten()
-                .or_else(|| row.try_get::<i16, _>(7).ok().flatten().map(|v| v as i32))
-                .or_else(|| row.try_get::<u8, _>(7).ok().flatten().map(|v| v as i32));
-            let dt_prec = row
-                .try_get::<i32, _>(8)
-                .ok()
-                .flatten()
-                .or_else(|| row.try_get::<i16, _>(8).ok().flatten().map(|v| v as i32))
-                .or_else(|| row.try_get::<u8, _>(8).ok().flatten().map(|v| v as i32));
-            let num_prec = row
-                .try_get::<i32, _>(5)
-                .ok()
-                .flatten()
-                .or_else(|| row.try_get::<i16, _>(5).ok().flatten().map(|v| v as i32))
-                .or_else(|| row.try_get::<u8, _>(5).ok().flatten().map(|v| v as i32));
-            let num_scale = row
-                .try_get::<i32, _>(6)
-                .ok()
-                .flatten()
-                .or_else(|| row.try_get::<i16, _>(6).ok().flatten().map(|v| v as i32))
-                .or_else(|| row.try_get::<u8, _>(6).ok().flatten().map(|v| v as i32));
-            let data_type = match base.to_lowercase().as_str() {
-                "varchar" => match max_len {
-                    Some(-1) => "varchar(max)".to_string(),
-                    Some(n) => format!("varchar({n})"),
-                    None => "varchar".to_string(),
-                },
-                "nvarchar" => match max_len {
-                    Some(-1) => "nvarchar(max)".to_string(),
-                    Some(n) => format!("nvarchar({n})"),
-                    None => "nvarchar".to_string(),
-                },
-                "varbinary" => match max_len {
-                    Some(-1) => "varbinary(max)".to_string(),
-                    Some(n) if n > 0 => format!("varbinary({n})"),
-                    _ => "varbinary".to_string(),
-                },
-                "char" | "nchar" | "binary" => match max_len {
-                    Some(n) if n > 0 => format!("{base}({n})"),
-                    _ => base,
-                },
-                "decimal" | "numeric" => match (num_prec, num_scale) {
-                    (Some(p), Some(s)) => format!("{base}({p},{s})"),
-                    _ => base,
-                },
-                "datetime2" | "datetimeoffset" | "time" => match dt_prec {
-                    Some(p) => format!("{base}({p})"),
-                    _ => base,
-                },
-                _ => base,
-            };
-            ColumnInfo {
-                name: row.get::<&str, _>(0).unwrap_or("").to_string(),
-                data_type,
-                is_nullable: row.get::<&str, _>(2).unwrap_or("NO") == "YES",
-                column_default: row.get::<&str, _>(3).map(|s| s.to_string()),
-                is_primary_key: row.get::<i32, _>(4).unwrap_or(0) == 1,
-                extra: row.get::<&str, _>(9).filter(|s: &&str| !s.is_empty()).map(|s: &str| s.to_string()),
-                comment: row.get::<&str, _>(10).filter(|s: &&str| !s.is_empty()).map(|s: &str| s.to_string()),
-                numeric_precision: num_prec,
-                numeric_scale: num_scale,
-                character_maximum_length: max_len,
-                enum_values: None,
-                ..Default::default()
-            }
-        })
-        .collect())
+    Ok(rows.iter().map(sqlserver_column_metadata_from_row).collect())
+}
+
+fn sqlserver_column_metadata_from_row(row: &Row) -> SqlServerColumnMetadata {
+    let base = row.get::<&str, _>(1).unwrap_or("").to_string();
+    let max_len = row
+        .try_get::<i32, _>(7)
+        .ok()
+        .flatten()
+        .or_else(|| row.try_get::<i16, _>(7).ok().flatten().map(|v| v as i32))
+        .or_else(|| row.try_get::<u8, _>(7).ok().flatten().map(|v| v as i32));
+    let dt_prec = row
+        .try_get::<i32, _>(8)
+        .ok()
+        .flatten()
+        .or_else(|| row.try_get::<i16, _>(8).ok().flatten().map(|v| v as i32))
+        .or_else(|| row.try_get::<u8, _>(8).ok().flatten().map(|v| v as i32));
+    let num_prec = row
+        .try_get::<i32, _>(5)
+        .ok()
+        .flatten()
+        .or_else(|| row.try_get::<i16, _>(5).ok().flatten().map(|v| v as i32))
+        .or_else(|| row.try_get::<u8, _>(5).ok().flatten().map(|v| v as i32));
+    let num_scale = row
+        .try_get::<i32, _>(6)
+        .ok()
+        .flatten()
+        .or_else(|| row.try_get::<i16, _>(6).ok().flatten().map(|v| v as i32))
+        .or_else(|| row.try_get::<u8, _>(6).ok().flatten().map(|v| v as i32));
+    let data_type = match base.to_lowercase().as_str() {
+        "varchar" => match max_len {
+            Some(-1) => "varchar(max)".to_string(),
+            Some(n) => format!("varchar({n})"),
+            None => "varchar".to_string(),
+        },
+        "nvarchar" => match max_len {
+            Some(-1) => "nvarchar(max)".to_string(),
+            Some(n) => format!("nvarchar({n})"),
+            None => "nvarchar".to_string(),
+        },
+        "varbinary" => match max_len {
+            Some(-1) => "varbinary(max)".to_string(),
+            Some(n) if n > 0 => format!("varbinary({n})"),
+            _ => "varbinary".to_string(),
+        },
+        "char" | "nchar" | "binary" => match max_len {
+            Some(n) if n > 0 => format!("{base}({n})"),
+            _ => base,
+        },
+        "decimal" | "numeric" => match (num_prec, num_scale) {
+            (Some(p), Some(s)) => format!("{base}({p},{s})"),
+            _ => base,
+        },
+        "datetime2" | "datetimeoffset" | "time" => match dt_prec {
+            Some(p) => format!("{base}({p})"),
+            _ => base,
+        },
+        _ => base,
+    };
+    let column = ColumnInfo {
+        name: row.get::<&str, _>(0).unwrap_or("").to_string(),
+        data_type,
+        is_nullable: row.get::<&str, _>(2).unwrap_or("NO") == "YES",
+        column_default: row.get::<&str, _>(3).map(|s| s.to_string()),
+        is_primary_key: row.get::<i32, _>(4).unwrap_or(0) == 1,
+        extra: row.get::<&str, _>(9).filter(|s: &&str| !s.is_empty()).map(|s: &str| s.to_string()),
+        comment: row.get::<&str, _>(10).filter(|s: &&str| !s.is_empty()).map(|s: &str| s.to_string()),
+        numeric_precision: num_prec,
+        numeric_scale: num_scale,
+        character_maximum_length: max_len,
+        enum_values: None,
+        ..Default::default()
+    };
+    SqlServerColumnMetadata {
+        column,
+        is_identity: row.get::<i32, _>(11).unwrap_or(0) == 1,
+        is_computed: row.get::<i32, _>(12).unwrap_or(0) == 1,
+        is_hidden: row.get::<i32, _>(13).unwrap_or(0) == 1,
+        generated_always_type: row.get::<i32, _>(14).unwrap_or(0),
+    }
 }
 
 fn sqlserver_columns_sql(schema: &str, table: &str) -> String {
     let s = schema.replace('\'', "''");
     let t = table.replace('\'', "''");
+    // COLUMNPROPERTY keeps hidden/generated flags separate and returns NULL on
+    // SQL Server versions that do not expose a newer property.
     format!(
         "SELECT c.name AS COLUMN_NAME, \
          ty.name AS DATA_TYPE, \
@@ -1621,7 +1647,11 @@ fn sqlserver_columns_sql(schema: &str, table: &str) -> String {
            WHEN ic.column_id IS NOT NULL THEN 'identity(' + CONVERT(VARCHAR(38), ic.seed_value) + ',' + CONVERT(VARCHAR(38), ic.increment_value) + ')' \
            ELSE NULL \
          END AS COLUMN_EXTRA, \
-         ep.value AS COLUMN_COMMENT \
+         ep.value AS COLUMN_COMMENT, \
+         CONVERT(INT, COLUMNPROPERTY(c.object_id, c.name, 'IsIdentity')) AS IS_IDENTITY, \
+         CONVERT(INT, COLUMNPROPERTY(c.object_id, c.name, 'IsComputed')) AS IS_COMPUTED, \
+         CONVERT(INT, COLUMNPROPERTY(c.object_id, c.name, 'IsHidden')) AS IS_HIDDEN, \
+         CONVERT(INT, COLUMNPROPERTY(c.object_id, c.name, 'GeneratedAlwaysType')) AS GENERATED_ALWAYS_TYPE \
          FROM sys.objects o \
          JOIN sys.schemas s ON s.schema_id = o.schema_id \
          JOIN sys.columns c ON c.object_id = o.object_id \
@@ -2442,6 +2472,16 @@ mod tests {
         assert!(sql.contains("c.is_computed = 1 THEN 'computed'"));
     }
 
+    #[test]
+    fn sqlserver_columns_sql_exposes_structured_generation_flags() {
+        let sql = sqlserver_columns_sql("dbo", "orders");
+
+        assert!(sql.contains("COLUMNPROPERTY(c.object_id, c.name, 'IsIdentity')"));
+        assert!(sql.contains("COLUMNPROPERTY(c.object_id, c.name, 'IsComputed')"));
+        assert!(sql.contains("COLUMNPROPERTY(c.object_id, c.name, 'IsHidden')"));
+        assert!(sql.contains("COLUMNPROPERTY(c.object_id, c.name, 'GeneratedAlwaysType')"));
+    }
+
     #[test]
     fn sqlserver_table_comment_sql_queries_extended_properties() {
         let sql = sqlserver_table_comment_sql("dbo", "users");
diff --git a/crates/dbx-core/src/schema.rs b/crates/dbx-core/src/schema.rs
index 7a79e3bf8..e5f78bddb 100644
--- a/crates/dbx-core/src/schema.rs
+++ b/crates/dbx-core/src/schema.rs
@@ -4467,6 +4467,22 @@ pub async fn get_columns_core(
     .await
 }
 
+pub async fn get_sqlserver_column_metadata_core(
+    state: &AppState,
+    connection_id: &str,
+    database: &str,
+    schema: &str,
+    table: &str,
+) -> Result<Vec<db::sqlserver::SqlServerColumnMetadata>, String> {
+    retry_metadata_connection(state, connection_id, Some(database), || async {
+        let pool_key = state.get_or_create_pool(connection_id, Some(database)).await?;
+        let connections = state.connections.read().await;
+        try_sqlserver!(connections, &pool_key, get_column_metadata, schema, table);
+        Err("SQL Server column metadata requires a native SQL Server connection".to_string())
+    })
+    .await
+}
+
 fn deduplicate_column_infos(columns: Vec<db::ColumnInfo>) -> Vec<db::ColumnInfo> {
     let mut result: Vec<db::ColumnInfo> = Vec::with_capacity(columns.len());
     for column in columns {
diff --git a/crates/dbx-core/tests/live_sqlserver_completion.rs b/crates/dbx-core/tests/live_sqlserver_completion.rs
index 458509d93..026c82ac8 100644
--- a/crates/dbx-core/tests/live_sqlserver_completion.rs
+++ b/crates/dbx-core/tests/live_sqlserver_completion.rs
@@ -65,6 +65,84 @@ fn live_sqlserver_config(id: &str, database: &str) -> dbx_core::models::connecti
     }
 }
 
+#[tokio::test]
+#[ignore = "requires DBX_LIVE_SQLSERVER_HOST/PORT/USER/PASSWORD pointing at a writable SQL Server database"]
+async fn live_sqlserver_column_metadata_marks_non_positional_insert_columns() {
+    let database = std::env::var("DBX_LIVE_SQLSERVER_DATABASE").unwrap_or_else(|_| "tempdb".to_string());
+    let host = std::env::var("DBX_LIVE_SQLSERVER_HOST").unwrap_or_else(|_| "127.0.0.1".to_string());
+    let port = std::env::var("DBX_LIVE_SQLSERVER_PORT").ok().and_then(|value| value.parse().ok()).unwrap_or(1433);
+    let user = std::env::var("DBX_LIVE_SQLSERVER_USER").unwrap_or_else(|_| "sa".to_string());
+    let password = std::env::var("DBX_LIVE_SQLSERVER_PASSWORD").expect("DBX_LIVE_SQLSERVER_PASSWORD");
+    let mut client =
+        dbx_core::db::sqlserver::connect(&host, port, &user, &password, Some(&database), None, Duration::from_secs(10))
+            .await
+            .expect("connect SQL Server");
+
+    let suffix = uuid::Uuid::new_v4().simple().to_string();
+    let computed_table = format!("dbx_insert_computed_{suffix}");
+    let temporal_table = format!("dbx_insert_temporal_{suffix}");
+    let history_table = format!("dbx_insert_history_{suffix}");
+    let create_computed = format!(
+        "CREATE TABLE dbo.[{computed_table}] (id int IDENTITY(1,1) NOT NULL, quantity int NOT NULL, doubled AS quantity * 2, note nvarchar(40) NOT NULL)"
+    );
+    let create_temporal = format!(
+        "CREATE TABLE dbo.[{temporal_table}] (\
+         id int IDENTITY(1,1) NOT NULL PRIMARY KEY, \
+         note nvarchar(40) NOT NULL, \
+         valid_from datetime2 GENERATED ALWAYS AS ROW START HIDDEN NOT NULL DEFAULT SYSUTCDATETIME(), \
+         valid_to datetime2 GENERATED ALWAYS AS ROW END HIDDEN NOT NULL DEFAULT CONVERT(datetime2, '9999-12-31 23:59:59.9999999'), \
+         PERIOD FOR SYSTEM_TIME (valid_from, valid_to)\
+         ) WITH (SYSTEM_VERSIONING = ON (HISTORY_TABLE = dbo.[{history_table}]))"
+    );
+
+    dbx_core::db::sqlserver::execute_query(&mut client, &create_computed).await.expect("create computed table");
+    dbx_core::db::sqlserver::execute_query(&mut client, &create_temporal).await.expect("create temporal table");
+    dbx_core::db::sqlserver::execute_query(
+        &mut client,
+        &format!("INSERT INTO dbo.[{computed_table}] VALUES (3, N'normal')"),
+    )
+    .await
+    .expect("insert while omitting identity and computed columns");
+    dbx_core::db::sqlserver::execute_query(
+        &mut client,
+        &format!("INSERT INTO dbo.[{temporal_table}] VALUES (N'temporal')"),
+    )
+    .await
+    .expect("insert while omitting identity and hidden temporal columns");
+
+    let computed = dbx_core::db::sqlserver::get_column_metadata(&mut client, "dbo", &computed_table)
+        .await
+        .expect("read computed metadata");
+    let temporal = dbx_core::db::sqlserver::get_column_metadata(&mut client, "dbo", &temporal_table)
+        .await
+        .expect("read temporal metadata");
+
+    dbx_core::db::sqlserver::execute_query(
+        &mut client,
+        &format!("ALTER TABLE dbo.[{temporal_table}] SET (SYSTEM_VERSIONING = OFF)"),
+    )
+    .await
+    .expect("disable system versioning");
+    dbx_core::db::sqlserver::execute_query(
+        &mut client,
+        &format!("DROP TABLE dbo.[{temporal_table}], dbo.[{history_table}], dbo.[{computed_table}]"),
+    )
+    .await
+    .expect("drop metadata probe tables");
+
+    let identity = computed.iter().find(|metadata| metadata.column.name == "id").expect("identity column");
+    let quantity = computed.iter().find(|metadata| metadata.column.name == "quantity").expect("normal column");
+    let doubled = computed.iter().find(|metadata| metadata.column.name == "doubled").expect("computed column");
+    let valid_from = temporal.iter().find(|metadata| metadata.column.name == "valid_from").expect("row start column");
+    let valid_to = temporal.iter().find(|metadata| metadata.column.name == "valid_to").expect("row end column");
+
+    assert!(identity.is_identity);
+    assert!(!quantity.is_identity && !quantity.is_computed && !quantity.is_hidden);
+    assert!(doubled.is_computed);
+    assert!(valid_from.is_hidden && valid_from.generated_always_type == 1);
+    assert!(valid_to.is_hidden && valid_to.generated_always_type == 2);
+}
+
 #[tokio::test]
 #[ignore = "requires DBX_LIVE_SQLSERVER_HOST/PORT/USER/PASSWORD pointing at a writable SQL Server database"]
 async fn live_sqlserver_execute_query_creates_schema() {
diff --git a/crates/dbx-web/src/main.rs b/crates/dbx-web/src/main.rs
index a75df6b08..ccd18fe6f 100644
--- a/crates/dbx-web/src/main.rs
+++ b/crates/dbx-web/src/main.rs
@@ -308,6 +308,7 @@ async fn main() {
         .route("/schema/sqlserver/linked-server-catalogs", get(routes::schema::list_sqlserver_linked_server_catalogs))
         .route("/schema/sqlserver/linked-server-schemas", get(routes::schema::list_sqlserver_linked_server_schemas))
         .route("/schema/sqlserver/linked-server-tables", get(routes::schema::list_sqlserver_linked_server_tables))
+        .route("/schema/sqlserver/column-metadata", get(routes::schema::get_sqlserver_column_metadata))
         .route("/schema/schemas", get(routes::schema::list_schemas))
         .route("/schema/tables", get(routes::schema::list_tables))
         .route("/schema/objects", get(routes::schema::list_objects))
diff --git a/crates/dbx-web/src/routes/schema.rs b/crates/dbx-web/src/routes/schema.rs
index 865f44806..1597bf7ce 100644
--- a/crates/dbx-web/src/routes/schema.rs
+++ b/crates/dbx-web/src/routes/schema.rs
@@ -111,6 +111,20 @@ pub async fn list_sqlserver_linked_server_tables(
     Ok(Json(serde_json::to_value(result).map_err(|e| AppError(e.to_string()))?))
 }
 
+pub async fn get_sqlserver_column_metadata(
+    State(state): State<Arc<WebState>>,
+    Query(q): Query<SchemaQuery>,
+) -> Result<Json<serde_json::Value>, AppError> {
+    let database = q.database.as_deref().unwrap_or("");
+    let schema = q.schema.as_deref().unwrap_or("");
+    let table = q.table.as_deref().unwrap_or("");
+    let result =
+        dbx_core::schema::get_sqlserver_column_metadata_core(&state.app, &q.connection_id, database, schema, table)
+            .await
+            .map_err(AppError)?;
+    Ok(Json(serde_json::to_value(result).map_err(|e| AppError(e.to_string()))?))
+}
+
 pub async fn list_schemas(
     State(state): State<Arc<WebState>>,
     Query(q): Query<SchemaQuery>,
diff --git a/packages/app-tests/insertValueHints.test.ts b/packages/app-tests/insertValueHints.test.ts
index 9f61cbfff..982bd348d 100644
--- a/packages/app-tests/insertValueHints.test.ts
+++ b/packages/app-tests/insertValueHints.test.ts
@@ -1,6 +1,7 @@
 import { strict as assert } from "node:assert";
 import { test } from "vitest";
 import { buildInsertValueHints, expandToSqlStatementWindow, parseInsertValueHints, parseInsertValueHintsInRanges, parseInsertValuesClauses } from "../../apps/desktop/src/lib/sql/insertValueHints.ts";
+import { insertValueHintColumnNames } from "../../apps/desktop/src/lib/sql/insertValueHintColumns.ts";
 
 test("maps explicit column list to single-row VALUES", () => {
   const sql = "INSERT INTO auth_user (id, password, last_login) VALUES (5, 'hash', NULL)";
@@ -68,6 +69,56 @@ test("resolves columns from table metadata when column list is omitted", () => {
   );
 });
 
+test("skips SQL Server identity columns when mapping multi-row VALUES without a column list", () => {
+  const sql = "INSERT INTO dbo.users VALUES (N'A', 1), (N'B', 2)";
+  const columns = insertValueHintColumnNames("sqlserver", [
+    { name: "id", is_identity: true },
+    { name: "name" },
+    { name: "status" },
+  ]);
+  const hints = parseInsertValueHints(sql, {
+    resolveTableColumns: () => columns,
+  });
+  assert.deepEqual(
+    hints.map((hint) => hint.column),
+    ["name", "status", "name", "status"],
+  );
+});
+
+test("skips SQL Server computed and temporal generated columns in positional hints", () => {
+  const columns = insertValueHintColumnNames("sqlserver", [
+    { name: "id", is_identity: true },
+    { name: "quantity" },
+    { name: "doubled", is_computed: true },
+    { name: "note" },
+    { name: "valid_from", is_hidden: true, generated_always_type: 1 },
+    { name: "valid_to", is_hidden: true, generated_always_type: 2 },
+  ]);
+
+  assert.deepEqual(columns, ["quantity", "note"]);
+});
+
+test("skips visible SQL Server generated columns in positional hints", () => {
+  assert.deepEqual(
+    insertValueHintColumnNames("sqlserver", [
+      { name: "name" },
+      { name: "valid_from", generated_always_type: 1 },
+      { name: "valid_to", generated_always_type: 2 },
+    ]),
+    ["name"],
+  );
+});
+
+test("keeps identity columns in positional hints for databases other than SQL Server", () => {
+  assert.deepEqual(
+    insertValueHintColumnNames("postgres", [
+      { name: "id", is_identity: true },
+      { name: "name" },
+    ]),
+    ["id", "name"],
+  );
+});
+
 test("returns no hints for INSERT ... SELECT", () => {
   const sql = "INSERT INTO users (id, name) SELECT id, name FROM staging";
   assert.deepEqual(parseInsertValueHints(sql), []);
diff --git a/src-tauri/src/commands/schema.rs b/src-tauri/src/commands/schema.rs
index 5f667be71..98eb7d905 100644
--- a/src-tauri/src/commands/schema.rs
+++ b/src-tauri/src/commands/schema.rs
@@ -300,6 +300,17 @@ pub async fn get_columns(
     dbx_core::schema::get_columns_core(&state, &connection_id, &database, &schema, &table).await
 }
 
+#[tauri::command]
+pub async fn get_sqlserver_column_metadata(
+    state: State<'_, Arc<AppState>>,
+    connection_id: String,
+    database: String,
+    schema: String,
+    table: String,
+) -> Result<Vec<db::sqlserver::SqlServerColumnMetadata>, String> {
+    dbx_core::schema::get_sqlserver_column_metadata_core(&state, &connection_id, &database, &schema, &table).await
+}
+
 #[tauri::command]
 pub async fn list_indexes(
     state: State<'_, Arc<AppState>>,
diff --git a/src-tauri/src/lib.rs b/src-tauri/src/lib.rs
index 79d4e55f8..d8295f047 100644
--- a/src-tauri/src/lib.rs
+++ b/src-tauri/src/lib.rs
@@ -1117,6 +1117,7 @@ pub fn run() {
             commands::schema::list_schema_infos,
             commands::schema::list_data_types,
             commands::schema::get_columns,
+            commands::schema::get_sqlserver_column_metadata,
             commands::schema::list_indexes,
             commands::schema::list_foreign_keys,
             commands::schema::list_triggers,