diff --git a/CHANGELOG.md b/CHANGELOG.md
index fe0a35c8a..6d9b82652 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,7 +10,8 @@ _When adding new entries to the changelog, please include issue/PR numbers where
 - Added support for `--output` option to `kart conflicts`. [#135](https://github.com/koordinates/kart/issues/135)
 - Bugfix: Better error message on using `kart conflicts -ogeojson` for `meta-item` conflicts. [#515](https://github.com/koordinates/kart/issues/515)
 - Removed the older `upgrade-to-tidy` and `upgrade-to-kart` features which were only relevant to Sno (predecessor of Kart). [[#585](https://github.com/koordinates/kart/issues/585]]
-- Added support for `--decorate` and `--no-decorate` in `kart log`. [[#586](https://github.com/koordinates/kart/issues/586]]
+- Added support for `--decorate` and `--no-decorate` in `kart log`. [#586](https://github.com/koordinates/kart/issues/586)
+- Bugfix: Fixed a bug where creating a MSSQL working copy fails when there are large (~10KB) geometries. [#617](https://github.com/koordinates/kart/issues/617)
 
 ## 0.11.1
 
diff --git a/kart/sqlalchemy/adapter/sqlserver.py b/kart/sqlalchemy/adapter/sqlserver.py
index 5388d89eb..c4c23e113 100644
--- a/kart/sqlalchemy/adapter/sqlserver.py
+++ b/kart/sqlalchemy/adapter/sqlserver.py
@@ -397,7 +397,8 @@ def sql_write(self, bindvalue):
         # POINT EMPTY is handled specially since it doesn't have a WKB value the SQL Server accepts.
         return sa.case(
             (
-                bindvalue == sa.literal_column(self.EMPTY_POINT_WKB),
+                sa.cast(bindvalue, sa.VARBINARY)
+                == sa.literal_column(self.EMPTY_POINT_WKB),
                 Function(
                     quoted_name("geometry::STGeomFromText", False),
                     "POINT EMPTY",
diff --git a/tests/data/large-geometry.tgz b/tests/data/large-geometry.tgz
new file mode 100644
index 000000000..4d6d34a48
Binary files /dev/null and b/tests/data/large-geometry.tgz differ
diff --git a/tests/test_working_copy_sqlserver.py b/tests/test_working_copy_sqlserver.py
index da484035d..6b214a9b0 100644
--- a/tests/test_working_copy_sqlserver.py
+++ b/tests/test_working_copy_sqlserver.py
@@ -655,3 +655,25 @@ def test_checkout_and_status_with_no_crs(
                 ]
             )
             assert r.exit_code == 0, r.stderr
+
+
+def test_checkout_large_geometry(
+    new_sqlserver_db_schema,
+    data_archive,
+    tmp_path,
+    cli_runner,
+):
+    repo_path = tmp_path / "repo"
+    repo_path.mkdir()
+
+    with data_archive("large-geometry") as repo_path:
+        with new_sqlserver_db_schema() as (sqlserver_url, sqlserver_schema):
+            r = cli_runner.invoke(["create-workingcopy", sqlserver_url])
+            r = cli_runner.invoke(
+                [
+                    "-C",
+                    str(repo_path),
+                    "status",
+                ]
+            )
+            assert r.exit_code == 0, r.stderr