--- a
+++ b/tests/support/mssql/entrypoint.sh
@@ -0,0 +1,65 @@
+#!/bin/bash
+
+set -euo pipefail
+
+if [ "$1" = '/opt/mssql/bin/sqlservr' ]; then
+  # If this is the container's first run, initialize the application
+  # database
+  if [ ! -f /tmp/app-initialized ]; then
+    # Initialize the application database asynchronously in a
+    # background process. This allows a) the SQL Server process to be
+    # the main process in the container, which allows graceful
+    # shutdown and other goodies, and b) us to only start the SQL
+    # Server process once, as opposed to starting, stopping, then
+    # starting it again.
+    function initialize_app_database() {
+        timeout=20
+        limit="$((SECONDS + timeout))"
+
+        # MSSQL doesn't apply the default collation specified in the
+        # MSSQL_COLLATION environment variable immediately on startup. So we
+        # need to wait for this to be applied before we create our application
+        # databases, otherwise we have a race-condition. We check the collation
+        # of "tempdb" as that's the system database whose collation affects us.
+        until [[ "$(get_tempdb_collation)" == "$MSSQL_COLLATION" ]]; do
+          sleep 1s
+          if [[ "${SECONDS}" -gt "${limit}" ]]; then
+            echo >&2 "Failed to connect to MSSQL and confirm collation setting after ${timeout} seconds"
+            echo >&2 "Expected collation: $MSSQL_COLLATION"
+            echo >&2 "Got: $(get_tempdb_collation)"
+            exit 1
+          fi
+        done
+
+        # Run the setup script to create the DB and the schema in the DB
+        _sqlcmd -i /mssql/setup.sql
+
+        # Note that the container has been initialized so future
+        # starts won't wipe changes to the data
+        touch /tmp/app-initialized
+    }
+
+    function get_tempdb_collation() {
+      # We need to set NOCOUNT so we don't get a "Rows affected" count in the output
+      _sqlcmd -Q "SET NOCOUNT ON; SELECT DATABASEPROPERTYEX('tempdb', 'Collation');"
+    }
+
+    function _sqlcmd() {
+      # Extra arguments:
+      #    -C : trust server certificate
+      #    -b : exit with 1 on error rather than 0
+      # -h -1 : no headers in output
+      #    -W : trim trailing whitespace
+      /opt/mssql-tools18/bin/sqlcmd \
+        -S localhost -U sa -P "$MSSQL_SA_PASSWORD" -d master \
+        -C -b -h -1 -W \
+        "$@"
+    }
+
+    initialize_app_database &
+  fi
+fi
+
+# The Docker library we're using hides stdout from us if the container exits with an error, so send everything to
+# stderr.
+exec "$@" 1>&2