thread Re: Messages from POS app / dashboard in Payments Troubleshooting

Messages from POS app / dashboard

tonydow — Sun, 21 Sep 2025 12:08:11 GMT

I have an ongoing support call with Square which I would like to outline here. I can send a message to a customer from the app but cannot send the same customer a message from the dashboard as it says they need to have made a purchase and received a digital invoice. Alongside this, anyone I message initially generates a statement that they do not allow responses which doesn’t make sense as I am probably replying to a query they have made. Any ideas?

Re: Messages from POS app / dashboard

tranguyen — Mon, 07 Sep 2020 10:13:42 GMT

Hi @tonydow, sorry to hear you are still experiencing an issue with this! I haven't come across anything like this before, so I'll need to take a look at the ticket that was created on your behalf.

From what I know, in order to start a conversation with a customer, the customer must have requested a digital receipt with their email address in order to be subscribed. That's the standard flow for transactions processed through the apps. To help me look into this on my end, can you let me know how the customer's profile was created - was it through the app or through an online transaction? That will definitely help me narrow it down.

Re: Messages from POS app / dashboard

tonydow — Mon, 07 Sep 2020 13:41:49 GMT

Hi Tra. Thanks for getting back to me. I have been through this with Support, screenshots etc.

Basically, the flow is this:

I get an email from Weebly notifying me that a customer has sent me a message (usually a question) from the Contact Us section of my website.

This generates an entry in my Customer Directory with the customers email which I can amend to add their name.

Using the POS app, I can send this customer a message addressing their query.

If I try to do this using the Dashboard, I can’t as the customer, at this point, hasn’t made a purchase.

I don’t understand why there has to be this criteria on sending a message using the Dashboard when I can send the same customer a message using the app.

If I look at the message I sent (using the app) on the Dashboard it states “This is a private message from your customer. This customer does not allow responses.”

The customer, at this point, has not had the option to opt out of responses. They also would be very unlikely to as they have just asked a question and would, presumably, want a reply.

I hope this explains the issue.

Regards, Tony

Re: Messages from POS app / dashboard

tranguyen — Mon, 07 Sep 2020 15:22:41 GMT

Thank you so much for sending on all that information, @tonydown! I know you've gone through a lot of different troubleshooting steps with our Support team already but I just want to get a better understanding of this issue myself.

I'm going to take the information above and reached out to our engineering team again to ask them for further clarification. Sorry this has taken longer than expected to be resolved Tony! Let me know if there is anything else I can do for you in the meantime.

Re: Messages from POS app / dashboard

tonydow — Mon, 07 Sep 2020 15:40:32 GMT

Thanks again Tra. I’ll leave it in your capable hands!

Re: Messages from POS app / dashboard

tranguyen — Thu, 10 Sep 2020 10:49:41 GMT

Thanks so much for your patience while our team work on this, @tonydow! The team have let me know this is an issue with how Square is reading conversations received from the Online site at the moment.

The expected behaviour is customers must requested a digital receipt with their email address in order to initiate the conversation (this explained the message you are seeing on your Dashboard). They are working on a fix for the flow of conversation within the Square Point of Sale app now but I don't have an exact date for this yet, so I'll be sure to follow-up again when I get an update.

For now, they recommend that for any query that come in before customers make a purchase, it's best to respond to them outside of Square. Once the customers have made a purchase from your Shop, you can take advantage of the messaging tool within Square.

Again, apology for all the inconvenience caused by this, Tony!

Re: Messages from POS app / dashboard

tonydow — Thu, 10 Sep 2020 11:08:19 GMT

Hi Tra. If only it was that simple! I have many customers that have made a purchase but I still cannot message them. It is very unlikely that they have opted out of responses so It must be the requirement to have requested a digital receipt. Why is this mandatory. It is very frustrating that I cannot interact with existing customers and even more so that I cannot interact with potential customers.

Regards, Tony

Re: Messages from POS app / dashboard

tranguyen — Thu, 10 Sep 2020 11:55:16 GMT

I completely understand your frustration and I'll be sure to feed it back to the team! If the customer has made a purchase through your site and you are still unable to message them, you can try adding the option to allow customers to opt-in to receiving emails from you. To do this:

1. Go to your Square Online site dashboard

2. Scroll down to Settings > Checkout

3. Click Edit on Advanced Settings

4. Tick the box next to "Allow customers to opt-in to receiving marketing emails from you"

5. Save

I hope this will help - if customers have opt in here during their purchase and you are still not able to message them, please let me know.

Re: Messages from POS app / dashboard

tonydow — Thu, 10 Sep 2020 17:03:15 GMT

Thank you Tra. I will certainly try this but I think the sticking point is the requirement to have requested a digital receipt. Is it REALLY

necessary to have done this before allowIng messages?

Re: Messages from POS app / dashboard

tonydow — Thu, 10 Sep 2020 17:18:02 GMT

Also, your suggestion to opt in to marketing emails could be counter productive. I, for one, would be unlikely to tick that box thinking I may get lots of marketing emails as opposed to standard interaction between customer and seller.

Re: Messages from POS app / dashboard

tranguyen — Fri, 11 Sep 2020 09:44:12 GMT

I completely understand your frustration, @tonydow. This is how the system is built at the moment -- it needs to see that the customer has made a purchase and opt in before message can be initiate. The digital receipt is the best way to prove that a purchase has happened.

I will be sure to pass your feedback to the appropriate team as well since it does look like there is an issue with how information is passed between Square and the Online site.

Re: Messages from POS app / dashboard

tonydow — Fri, 11 Sep 2020 09:57:33 GMT

Hi Tra. I appreciate that this is a system requirement and the explanations you have given. Can you explain why this is not the case when messaging from the app which doesn’t have such restrictions. Thanks

Re: Messages from POS app / dashboard

tranguyen — Fri, 11 Sep 2020 10:55:34 GMT

Hi @tonydow, The current flow in the Square Point of Sale app is actually a bug that our team are working on. It should be working the same way as the Dashboard (not being able to reply to message)

Re: Messages from POS app / dashboard

tonydow — Fri, 11 Sep 2020 12:37:32 GMT

Hi Tra. That’s not what I wanted to hear! At least, in the app, I can message potential customers, answer queries. If you fix this ‘bug’, that will be lost.

Re: Messages from POS app / dashboard

tranguyen — Thu, 24 Sep 2020 09:58:50 GMT

Hi @tonydow, thank you for your patience as we look into this! I've received further clarification from the team.

Even if a customer contacted you through the Contact Us form on your website, they need to explicitly opt-in to receiving emails from you in order for you to reply from both the Dashboard and the app.

You'll need to enable opt-in checkbox within your Contact Us section to ensure that you can reply to customers within Square. I understand that the wording may not reflect the true nature of the interaction, but this is the only way at the moment.

You should see the option within the Settings of your Contact Us section.

Once you've toggled the option to blue and republished the site, the changes will appear.

Re: Messages from POS app / dashboard

tonydow — Thu, 24 Sep 2020 14:34:01 GMT

Thanks Tra. I have enabled that but really don’t like the wording about marketing and promotional materials. Surely it would be a minor thing to change this wording to ‘Opt in to further communication’ or words to that effect.

Re: Messages from POS app / dashboard

tranguyen — Fri, 25 Sep 2020 09:20:32 GMT

Completely understandable @tonydow! I've passed your feedback to the appropriate team for considerations. Now that the opt-in is enable, let me know if you are still running into trouble replying to customers.