diff --git a/test/tw-2563.t b/test/tw-2563.t
new file mode 100755
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+++ b/test/tw-2563.t
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+#!/usr/bin/env bash
+# This tests the migration path from 2.5.3 or earlier to 2.6.0 with respect to
+# the upgrade of the status field from waiting to pending
+. bash_tap_tw.sh
+
+# Setup
+task add Actionable task wait:yesterday
+task add Non-actionable task wait:tomorrow+1h
+
+# Simulate this was created in 2.5.3 or earlier (status is equal to waiting,
+# not pending)
+sed -i 's/pending/waiting/' $TASKDATA/pending.data
+
+# Trigger upgrade
+task all
+
+# Assertion: Exactly one task is considered waiting
+[[ `task +WAITING count` == "1" ]]
+
+# Report file content
+echo pending.data
+cat $TASKDATA/pending.data
+echo completed.data
+cat $TASKDATA/completed.data
+
+# Assertion: No lines in data files with "waiting" status
+[[ -z `cat $TASKDATA/pending.data | grep waiting` ]]
+[[ -z `cat $TASKDATA/completed.data | grep waiting` ]]
+
+# Assertion: No tasks were moved into completed.data
+[[ `cat $TASKDATA/pending.data | wc -l` == "2" ]]
+[[ `cat $TASKDATA/completed.data | wc -l` == "0" ]]