diff --git a/coderd/database/db.go b/coderd/database/db.go
index 6d5ad99576..8a3a6f1055 100644
--- a/coderd/database/db.go
+++ b/coderd/database/db.go
@@ -182,7 +182,7 @@ func (q *sqlQuerier) InTx(function func(Store) error, txOpts *TxOptions) error {
 }
 
 // InTx performs database operations inside a transaction.
-func (q *sqlQuerier) runTx(function func(Store) error, txOpts *sql.TxOptions) error {
+func (q *sqlQuerier) runTx(function func(Store) error, txOpts *sql.TxOptions) (err error) {
 	if _, ok := q.db.(*sqlx.Tx); ok {
 		// If the current inner "db" is already a transaction, we just reuse it.
 		// We do not need to handle commit/rollback as the outer tx will handle
diff --git a/coderd/database/db_test.go b/coderd/database/db_test.go
index 9941ef5ba3..bec132e0fb 100644
--- a/coderd/database/db_test.go
+++ b/coderd/database/db_test.go
@@ -5,9 +5,11 @@ import (
 	"database/sql"
 	"testing"
 
+	"github.com/DATA-DOG/go-sqlmock"
 	"github.com/google/uuid"
 	"github.com/lib/pq"
 	"github.com/stretchr/testify/require"
+	"golang.org/x/xerrors"
 
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/dbtestutil"
@@ -82,6 +84,33 @@ func TestNestedInTx(t *testing.T) {
 	require.Equal(t, uid, user.ID, "user id expected")
 }
 
+func TestInTx_CapturesRollbackError(t *testing.T) {
+	t.Parallel()
+
+	sqlDB, mock, err := sqlmock.New()
+	require.NoError(t, err)
+	t.Cleanup(func() { _ = sqlDB.Close() })
+
+	db := database.New(sqlDB)
+
+	callbackErr := xerrors.New("callback failed")
+	rollbackErr := xerrors.New("rollback failed")
+
+	mock.ExpectBegin()
+	mock.ExpectRollback().WillReturnError(rollbackErr)
+
+	err = db.InTx(func(_ database.Store) error {
+		return callbackErr
+	}, nil)
+	require.EqualError(t, err, "defer (rollback failed): execute transaction: callback failed")
+	require.ErrorIs(t, err, callbackErr,
+		"returned error should still match the callback error when rollback fails")
+	require.NotErrorIs(t, err, rollbackErr,
+		"rollback failure should be reported in the message, not wrapped in the error chain")
+
+	require.NoError(t, mock.ExpectationsWereMet())
+}
+
 func testSQLDB(t testing.TB) *sql.DB {
 	t.Helper()
 
diff --git a/go.mod b/go.mod
index f4c5d57268..7dcd74dbf2 100644
--- a/go.mod
+++ b/go.mod
@@ -105,6 +105,7 @@ replace github.com/openai/openai-go/v3 => github.com/kylecarbs/openai-go/v3 v3.0
 require (
 	cdr.dev/slog/v3 v3.0.0
 	cloud.google.com/go/compute/metadata v0.9.0
+	github.com/DATA-DOG/go-sqlmock v1.5.2
 	github.com/Microsoft/go-winio v0.6.2
 	github.com/acarl005/stripansi v0.0.0-20180116102854-5a71ef0e047d
 	github.com/adrg/xdg v0.5.0
diff --git a/go.sum b/go.sum
index 5374bc9af4..4037a81e94 100644
--- a/go.sum
+++ b/go.sum
@@ -796,6 +796,7 @@ github.com/kirsle/configdir v0.0.0-20170128060238-e45d2f54772f h1:dKccXx7xA56UNq
 github.com/kirsle/configdir v0.0.0-20170128060238-e45d2f54772f/go.mod h1:4rEELDSfUAlBSyUjPG0JnaNGjf13JySHFeRdD/3dLP0=
 github.com/kisielk/errcheck v1.5.0/go.mod h1:pFxgyoBC7bSaBwPgfKdkLd5X25qrDl4LWUI2bnpBCr8=
 github.com/kisielk/gotool v1.0.0/go.mod h1:XhKaO+MFFWcvkIS/tQcRk01m1F5IRFswLeQ+oQHNcck=
+github.com/kisielk/sqlstruct v0.0.0-20201105191214-5f3e10d3ab46/go.mod h1:yyMNCyc/Ib3bDTKd379tNMpB/7/H5TjM2Y9QJ5THLbE=
 github.com/klauspost/compress v1.18.5 h1:/h1gH5Ce+VWNLSWqPzOVn6XBO+vJbCNGvjoaGBFW2IE=
 github.com/klauspost/compress v1.18.5/go.mod h1:cwPg85FWrGar70rWktvGQj8/hthj3wpl0PGDogxkrSQ=
 github.com/klauspost/cpuid/v2 v2.2.10 h1:tBs3QSyvjDyFTq3uoc/9xFpCuOsJQFNPiAhYdw2skhE=