diff --git a/pkg/sql/importer/import_processor_planning.go b/pkg/sql/importer/import_processor_planning.go
index bca3aab66abe..011238078201 100644
--- a/pkg/sql/importer/import_processor_planning.go
+++ b/pkg/sql/importer/import_processor_planning.go
@@ -32,9 +32,12 @@ import (
 	"github.com/cockroachdb/cockroach/pkg/sql/sem/tree"
 	"github.com/cockroachdb/cockroach/pkg/sql/types"
 	"github.com/cockroachdb/cockroach/pkg/util/ctxgroup"
+	"github.com/cockroachdb/cockroach/pkg/util/log"
 	"github.com/cockroachdb/cockroach/pkg/util/protoutil"
 	"github.com/cockroachdb/cockroach/pkg/util/syncutil"
+	"github.com/cockroachdb/cockroach/pkg/util/timeutil"
 	"github.com/cockroachdb/cockroach/pkg/util/tracing"
+	"github.com/cockroachdb/logtags"
 )
 
 var replanThreshold = settings.RegisterFloatSetting(
@@ -217,8 +220,9 @@ func distImport(
 		}
 	}
 
+	flowCtx, watcher := newCancelWatcher(ctx, 3*progressUpdateInterval)
 	recv := sql.MakeDistSQLReceiver(
-		ctx,
+		flowCtx,
 		sql.NewMetadataCallbackWriter(rowResultWriter, metaFn),
 		tree.Rows,
 		nil, /* rangeCache */
@@ -238,6 +242,10 @@ func distImport(
 	stopProgress := make(chan struct{})
 
 	g := ctxgroup.WithContext(ctx)
+	g.GoCtx(func(ctx context.Context) error {
+		watcher.watch(ctx, recv)
+		return nil
+	})
 	g.GoCtx(func(ctx context.Context) error {
 		tick := time.NewTicker(time.Second * 10)
 		defer tick.Stop()
@@ -260,6 +268,13 @@ func distImport(
 	g.GoCtx(func(ctx context.Context) error {
 		defer cancelReplanner()
 		defer close(stopProgress)
+		defer watcher.stop()
+
+		if testingKnobs.beforeRunDSP != nil {
+			if err := testingKnobs.beforeRunDSP(); err != nil {
+				return err
+			}
+		}
 
 		if testingKnobs.beforeRunDSP != nil {
 			if err := testingKnobs.beforeRunDSP(); err != nil {
@@ -269,7 +284,7 @@ func distImport(
 
 		// Copy the evalCtx, as dsp.Run() might change it.
 		evalCtxCopy := *evalCtx
-		dsp.Run(ctx, planCtx, nil, p, recv, &evalCtxCopy, testingKnobs.onSetupFinish)
+		dsp.Run(flowCtx, planCtx, nil, p, recv, &evalCtxCopy, testingKnobs.onSetupFinish)
 		return rowResultWriter.Err()
 	})
 
@@ -282,6 +297,79 @@ func distImport(
 	return res, nil
 }
 
+// cancelWatcher is used to handle job PAUSE and CANCEL
+// gracefully.
+//
+// When the a job is canceled or paused, the context passed to the
+// Resumer is canceled by the job system. Rather than passing the
+// Resumer's context directly to our DistSQL receiver and planner, we
+// instead construct a new context for the distsql machinery and watch
+// the original context for cancelation using this cancelWatcher.
+//
+// When the cancelWatcher sees a cancelation on the watched context,
+// it informs the DistSQL receiver passed to watch by calling
+// SetError. This gives the DistSQL flow a chance to drain gracefully.
+//
+// However, we do not want to wait forever. After SetError is called,
+// we wait up to `timeout` before canceling the context returned by
+// newCancelWatcher.
+type cancelWatcher struct {
+	watchedCtx context.Context
+	timeout    time.Duration
+
+	done   chan struct{}
+	cancel context.CancelFunc
+}
+
+// newCancelWatcher constructs a cancelWatcher. To start the watcher
+// call watch. The context passed to newCancelWatcher will be watched
+// for cancelation. The returned context should be used for the
+// DistSQL receiver and DistSQLPlanner.
+func newCancelWatcher(
+	ctxToWatch context.Context, timeout time.Duration,
+) (context.Context, *cancelWatcher) {
+	ctx, cancel := context.WithCancel(
+		logtags.AddTags(
+			context.Background(),
+			logtags.FromContext(ctxToWatch)))
+	return ctx, &cancelWatcher{
+		watchedCtx: ctxToWatch,
+		timeout:    timeout,
+
+		done:   make(chan struct{}),
+		cancel: cancel,
+	}
+}
+
+// watch starts watching the context passed to newCancelWatcher for
+// cancellation and notifies the given DistSQLReceiver when a
+// cancellation occurs.
+//
+// After cancellation, if the watcher is not stopped before the
+// configured timeout, the context returned from the constructor is
+// cancelled.
+func (c *cancelWatcher) watch(ctx context.Context, recv *sql.DistSQLReceiver) {
+	select {
+	case <-c.watchedCtx.Done():
+		recv.SetError(c.watchedCtx.Err())
+		timer := timeutil.NewTimer()
+		defer timer.Stop()
+		timer.Reset(c.timeout)
+		select {
+		case <-c.done:
+		case <-timer.C:
+			timer.Read = true
+			log.Warningf(ctx, "watcher not stopped after %s, canceling flow context", c.timeout)
+			c.cancel()
+		}
+	case <-c.done:
+	}
+}
+
+func (c *cancelWatcher) stop() {
+	close(c.done)
+}
+
 func getLastImportSummary(job *jobs.Job) roachpb.BulkOpSummary {
 	progress := job.Progress()
 	importProgress := progress.GetImport()