I thought this would be simple UI task; the user can select an off-peak time for software updates to occur on their devices. This is for a IoT software deployment which may reboot the devices out in the field, taking them out of service for 10+ minutes.

Easy (pick a start time and install window length). This will work 90% of the time - most devices will apply the update during this slot & the process is done.

However for devices which are offline/busy during the install window, I need to allow an extra option; if the update does not occur during the slot ('tonight 2:00 to 4:00'), then allow a 'Retry' option. So try the installation again over the same time slot until it eventually applies or operator deals (via alerts/reporting) a terminal that is not updating.

Testing the dialog below with real users, had at least 2 users (out of 5 asked) completely misunderstand the dialog and how 'retry' works. I could fiddle with wording/explanation text, but wondering if I am missing something here? Is it really not obvious? I think if I have to add more explanation, then the UI is not self-explanatory enough.

Current dialog for scheduling update slot

There has been a few questions like this asked here, but most of them relate to setting up appointments in a calendar, so cannot find any applicable UI setting a precedent.

  • Actually, fiddling may be what is required here. I certainly didn't pick up from the dialog that the retry would occur every following day until successful (or obsolete). The "tomorrow" seems the obstacle. More importantly though: did you ask those 2 users what they took the dialog to mean? And what does that tell you about what needs to be changed? Mar 10, 2016 at 7:16
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    I think your terminology is too jargon heavy. "Update window", "will reoccur", etc. How about just: "Try again at the same time every day until the update succeeds" ? Mar 10, 2016 at 9:22
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    Does this have to be done for every update? How many days in advance is realistic? (I’d guees no more than a week, so relative dates like ‘today’, ‘tomorrow’, ‘Monday’ or ‘weekend’ should be used.) You’re using the word ‘retry’, but never ‘try’ for the first attempt, so it isn’t clear that this may fail. What would happen if ‘Auto Retry‘ was turned off – the update is never installed?
    – Crissov
    Mar 10, 2016 at 12:30
  • Feedback from the 2 users was 'I though retry would occur immediately if first attempt failed' and 'I though retry would occur every 2 hours' I will try and reword dialog and mock up a new improved version with feedback Yes, we ask the question every update, as this is part of a sequence of dialogs asking which devices, which update etc. Typical updates are 'Now', 'Tonight' or a future date when you want some new functionality to go live - like 1 Jan. And yes, the old system, you set a begin/end time and if the window was missed.. the update is never installed.
    – GrantB
    Mar 11, 2016 at 0:07

1 Answer 1


one thing that might be confusing is there is no indication of a recurrence. Also the label "start time" with a set date under doesn't make sense.

If it's suppose to be recurring, you should let the user select a day of the week instead of a date

  • Thanks for the answer. No indication of recurrence.. ummh, I thought the 'update will retry tomorrow.. ' would cover that, but could change wording to something like 'Will reoccur at the same time daily until update succeeds'? 'Start time' perhaps should be 'Start on' or similar, so I will take that suggestion. Allowing user to select day of the week, does not really work as if I said 'Monday' it would imply that it would try Mondays only; but I want it to retry on consecutive days during the timeslot until done.
    – GrantB
    Mar 10, 2016 at 4:30

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