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New & Improved Email Delivery System

Update August, 2011: Since launching several new features in conjunction with a commercial email delivery partner, we found that we were able to deliver emails more reliably and with less latency by sending the emails ourselves. At this point, Harvest has returned to sending emails directly from our own email servers.

Update June 15, 2011: the new email system has been launched!

Harvest sends hundreds of thousands of emails each week on behalf of our customers and 99% of those emails are delivered successfully. The remaining 1% can run into problems – sometimes messages are quarantined, spammed, or trashed on the receivers’ end. Our customers depend on Harvest to track time, then invoice for all those billable hours – and it’s critical that the invoice emails reach the customers’ inbox.

We have worked with several customers, their email providers, and our hosting provider and we’ve completely overhauled our email delivery system, which is launching early next week. This new system should ensure a much higher email delivery rate – and there are a few changes that will impact your workflow.

Unified Sender Email Address

The most significant change is that each email you send to your client via Harvest will no longer be “from” your email address. With the new email system, each Harvest email will be from "Your Name” <>. The reply-to field of each message will remain your email address – so your customer can still easily reply to the email message and get back to you as they would normally.

There is a technical reason for this change. Before the new system, Harvest would “whitelabel” the sender email address of each email (i.e. the “From” of each invoice email is from your own email address). This meant that there was simply no way for a system receiving the email from Harvest to verify Harvest as the sender of the email, since the email was “from” your own email address. Sometimes this was sufficient for receiving mail systems to discard the incoming email. With the new system, the receiving email system can look at Harvest’s DNS records (SPF DKIM for the technically minded), certain cryptographic headers in the email itself, and validate that the sender is who they claim to be, ie: Harvest.

Customizable Sender Profiles

With the new set up, we are launching a new feature for you to create different sender profiles, under Invoices > Configure:


You can create different sender profiles, such as: “Accounts Receivable” <> – and you can choose to send your invoice from that name, and the reply-to address will be the email you provide.

Note that the email address has to be valid, and Harvest does not set up the email address for you.

Improved Handling of Bounced Messages

With our previous setup, we have no way of telling if an email bounced. With this new system, if an email bounces from your client’s email provider, we can now detect it right away and let you know.
What are some possible reasons why an email bounces? A mistyped email address, a full mailbox, client is out of the office, or problems with mail servers. It doesn’t happen often, but when it does, Harvest will email you to let you know that the message has been bounced. We will also record the incident under the Invoice History section of that particular invoice.

Apart from the obvious benefits of this new email system, there are a couple of under-the-hood benefits which we believe will make Harvest’s mail capabilities truly world class.

Internal queuing of outbound email

Before handing the outbound emails off to the final delivery service, the new Harvest mail system will first create a queued version of the outbound email on the Harvest systems. This robust system will allow Harvest to resend messages which fail due to any upstream provider issues as well as retry the delivery of email using different services, if required.

More to Come

We will be monitoring the progress of our new email system and we’re striving for the highest deliverability possible. There will be more tweaks and improvements under the hood; the goal is to have a solid mail system, so you can rest easy knowing that all important client messages are delivered. In the near future, we will also be looking at more features on the user front, so you can tell if a client indeed viewed the email message or invoice.

Thank you for your continued support, and please let us know if you have any questions or feedback!

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This was posted in New Features, Online Invoicing, Product News.
  • theFreelanceDesigner on June 10, 2011

    Excellent. Harvest continues to be the best overall solution for running a small business.

  • Good news and timing. I just had this issue with one of my clients not receiving my invoices

  • Ivan Radisson on June 10, 2011

    I have a question:

    So the new emails will be sent from by default but there will be an option for those who really want to send “from” their own address?

    Is this right?

  • This is fabulous. I just requested this feature last week.

    Thanks for continually working to improve this wonderful service!

  • This is great news. I had an email that was not being delivered to one address, and it was because their SMTP server was doing domain lookups based on the from address, and the IP address of Harvests’ SMTP server and because it looked like the email was being spoofed, it was never delivered.

    I did not know this, and ended up using the postal methods to send the invoice via snail mail (which is a nice option, BTW).

    @IVAN — I *think* the reply to will still be your email address, but for everything to work smoothly, I *think* the from address must have the domain name of the SMTP server sending the email, which is the harvest server in this case. The SMTP server on the receiving end probably looks up the PTR record of the harvest SMTP server and sees that the IP address is really what the from email domain says it is, and if its your domain name in the email, it would not deliver it, since the harvest SMTP server IP is not going to be the same as your domain name IP. Again, this is what I *think* is happening, but I’m sure someone from harvest will chime in, and make things clear.

    Best of luck with everything,

  • charlie arehart on June 10, 2011

    Very good to hear, indeed. Of course, with any significant change, there’s the chance that something may go amiss, but let’s hope it all goes well.

  • charlie arehart on June 10, 2011

    @Bruce, I think what Ivan is asking, “what if I don’t want to have the mail be ‘from’ harvest, despite these benefits? what if I don’t think I ever suffered the problem and fear I might hit another?”

    It doesn’t seem that Harvest is allowing for that. The key sentence seems to be, “You can create different sender profiles, such as: “Accounts Receivable” – and you can choose to send your invoice from that name, and the reply-to address will be the email you provide.”

    One might read that to suggest the profiles would let you override things. I don’t see it saying that. It seems the FROM address will not be changed to that, only the reply-to. (If it had 2 fields, or a button to indicate to use the one address for both, then it might be that such an override was possible.)

    But it may be that all the other things in the change (especially the use of Postmark and such) mean that now they *cannot* let you specify a from address other than one in the harvest domain (even if you wanted it to).

    Let’s see what the Harvest folks say. My sense is that it will not be allowed, and that they feel the benefits of the new setup far outweigh the risks.

  • Charlie Arehart: I’m sure you’re right in your reading of this.

    Harvest: I love your attitude of innovating/sorting issues BUT having an option to ‘send from’ my email address would be preferable for us.

    Having our brand reinforced whenever possible is always our preference, and whilst I’m sure people know we use 3rd party apps/suppliers, white label is always what we go for (and pay more for the pleasure in some cases)…

  • @Bruce, @charlie – one way around this would be for harvest to allow emails to be sent through our own email servers much like an email client would be configured to setup to send emails via SMTP. That would be the best way to implement it, but it would take away some of the simplicity of the application (which is one if its greatest features).

  • Great news, thanks for doing this!

  • Doug Fales on June 10, 2011

    Thanks for your comments and questions everyone. I just want to clarify some things from the original post before I answer individual questions.

    First, there are two parts of a From address: 1) the display name and 2) the actual email address. For example, with an address like “Harvest Billing Dept “, the display name is “Harvest Billing Dept” and the address is “”

    As part of our switch to a commercial delivery partner, we must limit the email address part of the From address to a specific, verified address. This is a small tradeoff to ensure much higher deliverability to all recipients, regardless of their email provider.

    Following along with the above address as an example, this means that your emails will go out with addresses like so:

    From: Harvest Billing Dept
    Reply-To: Harvest Billing Dept

    In many modern email clients, the display name will be most visible (many clients hide the actual address if a display name is present). This means you will get some degree of white label by just including a descriptive display name in your sender profile. We did this intentionally to help offset the effect of using a single From address for all invoice and estimate emails. Replies will still go to your address, even though the origin address is in the domain.

    Now, to some specific answers…

    @Ivan The actual From email part will be The display name will either be the display name you have chosen for your sender profile or the full name of your Harvest user (if you have no sender profile configured).

    @Bruce You’re exactly right about the delivery issues related to using different sender addresses. This is one of the main reasons we have decided to use a commercial email delivery partner.

    @Charlie That’s correct–the limitation of using only is something that comes with using a delivery partner.

    @Jon We definitely understand that there is a sacrifice here in terms of not having 100% white label. By allowing you to customize the display name of the From address, we hope that in most cases your recipients will not notice that the actual email address is not located at your domain. In addition, their replies will always go to your address, and not to the verified sender address.

    We completely understand the sensitive nature of any change in email service, and it is our goal to make this transition smoothly, and in a way that gives you more reliable deliverability of Harvest messages. Thanks again everyone for your excellent feedback and questions!

  • Yay! Many of my clients were not getting their invoices so this is great news. They would always go to their SPAM folders.

  • Michael Moore on June 10, 2011

    Wonderful! Like an idiot I mistyped an email address and the accounting department wasn’t getting my invoices.

    Thank you for saving me from myself!

  • Still think it would be very easy to have a configuration option to allow for a choice of email methods:

    1. Harvest Delivery Method
    2. Self Hosted Delivery Method (by specifying our own mail server)

  • @david It’s not technically impossible, but it does add a pretty big layer of complexity when you’re trying to troubleshoot things.

    “My invoices aren’t getting through to my clients” then becomes a back and forth between multiple organizations (Harvest, ISPs, in-house IT staff/individuals) trying to figure out where the breakdown is happening.

  • @J Lane – understood, but some of us have already setup mail servers appropriately to avoid the exact issues that Harvest has now resolved for its clients.

    It’s not a show stopper for us, but it certainly should be an option.

    The simplest thing to do from the support point of view is to just state the options. Harvest will not guarantee delivery when the Self Hosted option is selected. I might even go as far as saying we will not debug email delivery issues unless the “Harvest Delivery Method” is selected. Even go as far as making it very clear right on the screen that has the options that your email is in danger of not being delivered if you select the Self Hosted option.

    We are a support organization ourselves so I know the challenges you refer to in diagnosing email issues. If it wasn’t for spammers email deliverability would be so much easier to manage.

  • Praise overall on the strategy to use PostMark for outbound email.

    Might I suggest you have your tech peeps check in with Zendesk tech people in regard to sending outbound email on behalf of another domain – with full SMTP security standards followed. They do it from Zendesk, and since you provide the sub-domain model here at Harvest (e.g. – it might be a reasonable feature feature to offer.

    Please feel free to contact me with any questions.

    James McFarland, owner at arrochar software llc
    super happy Harvest customer.

  • Trevor Gehman on June 13, 2011

    Great job. Just want to lend my support to your decisions. Definitely think you made the right ones in your implementation.

  • Brian J. on June 13, 2011

    I’m in strong support of James McFarland’s idea and the general idea of white labeling. I’d pay $5-$10 extra/mo extra (and be happy to configure the SPF/DNS records on our end) to ensure that mail came from my domain only.

    I’d also be happy to take my chances with the old delivery method if that were an option, and would be happy with Harvest not taking responsibility for failed email delivery – something that’s never happened to us.

    I do love Harvest but it definitely screams “small time” to have our invoices come from the harvestapp domain. It’s not quite as bad as using a gmail address for business but it does come close.

  • Great, look forward.

    Is their also an option to see if people did read the mail / follow the link?
    Especially for Estimates, it would be great if you could see that people did open it.

    I thinks this is a very small change to add, but really nice to have.

  • Good News…

    Can I ask when this change is expected to go live?


  • Great news, not that it happened a lot but a few never reached the intended client, this is a good sensible and beneficial change to the service. Keep up the good work.

  • Doug Fales on June 14, 2011

    @Mal This change was deployed at about 3PM EDT today.

    @Brian @James and @David: Thanks for your ideas about a user-hosted mail server option. This is something we considered when building out the existing system but decided to skip on this first iteration. We will certainly keep your suggestions in mind when it’s time for the next round of improvements on our email system.

    @Flip Great point! Open/Read tracking is something we’d like to eventually offer for crucial messages like invoices and estimates. It’s definitely on our radar.

    Thanks everyone for your comments and suggestions. Keep them coming!

  • I’m glad to see this. I had quit sending invoice to clients via Harvest since they weren’t getting there. I am surprised to hear that 99% of harvest emails were getting delivered. It was more like 75% for me.

    I just had Harvest send them to me, and I’d use the email client to edit the email as a new email, type in the client’s addr, and away they went. It took all of five seconds per client.

    This would also work for those folks who don’t want to appear “small time” by having invoices arrive from the harvest domain.

  • Cade Roux on June 15, 2011

    I’ve had a lot of trouble with invoices not arriving at the client (although fine at my personal email) since I switched to Harvest from Freckle.

    And while I’m happier with Harvest and am planning on switching to a paid Harvest plan, the new email system just completely failed to send an invoice to three different addresses on two domains).

    I was really looking forward to the new system, but I think I’m going to be doing PDF as manual attachments until I get some kind of confidence in the new system.

  • Cade Roux on June 15, 2011

    Well, the email just arrived at two of the addresses, so I’ll retract some of that last comment – I’ll have to check on the problem client address still.

    I guess there’s more of a delay (a few minutes) in the new mailing system.

  • Just sent and invoice and I got the CC – that is proof that it works as before Postini would always catch them!

    However, (using an iPad) if I reply – it wants to go back to notifications@ and this is the same on the iPhone too…

    Having done a reply (to test) I received a reply from Harvest saying that it’s an unmonitored mailbox blah blah…

    I guess this is not by design?


  • Nice work mates. I keep loving Harvest!

  • I appreciate your effort, but I really don’t like these changes…

  • I can see why you would do this if delivery was a problem. But after just a few minutes in the new system, I am already very dissatisfied with the lag time just from queuing up emails before sending. I’m waiting on the invoice to show up in my inbox and it’s apparently stuck in your queue some place.

    As someone who never had any delivery problems *until now*, this is pretty disheartening. On a regular day, I won’t know if forgot to click “Send a copy to me” or if it’s stuck in your queue. It’s going to add a big unknown to a system that was functioning fine for me previously…

  • @Mal Postini is one of the troublesome systems we designed our new mail system to be able to effectively deliver to. Could you send some details of your reply-to issues to We are unable to reproduce this but will investigate.

    @Cade and @Chris Sorry to hear you are experiencing delayed emails. We have prioritized reliable email delivery with this project. Our goal was to make sure emails had the best chance of delivery, and make sure emails are never lost if there is a delivery or provider issue. Now that we have a robust framework in place we will tune the system to speed up delivery times. On the whole delivery lag time has been low (or undetectable) but we have seen sporadic periods where emails could take 60s+ to arrive at their recipients. Don’t worry, we will work to reduce this lag and will keep you updated.

    @Juanjo Sorry you don’t like the changes. Do you have some specific feedback?

  • charlie arehart on June 16, 2011

    @Chris, you’ve not said how long you had to wait. Is it that it was nearly instance before, and now there’s a “lag” of perhaps a minute or two? If so, it’s perhaps just that there is now some spooling on the server end (at Harvest). That’s not that unusual. Many other email systems do also take at least a minute or so to get out. Chris, if it wasn’t much more than that, do you think you could just adjust your expectations? Trying to help, not criticizing.

    @Warwick, to address his doubt of whether the email was sent, do you guys envision offering any insight into the status of emailing? Whether it’s still in the queue, or been sent? The announcement indicated plans to be able to detect/handled failed emails. It just isn’t clear if you’re planning to expose this info to us.

  • @charlie. I’m a web professional and don’t need lectures about standard email delivery times. I had time to notice the delay, re-read the thread, compose a response and still not have the emails — though I did not time it.

    Do you work for Harvest? Or are you just trying to be helpful? It would seem bizarre if Harvest was asking me to degrade my expectations at the point that they are upgrading their services. @warwick’s official response was much more satisfactory and appropriate in acknowledging the problem.

  • charlie arehart on June 16, 2011

    @Chris, dude, chill. Did you not see my last sentence in the response to you, “Trying to help, not criticizing.” They were simple questions, just trying to help you, Harvest, and readers understand the situation more clearly.

    No, I don’t work for Harvest. Yes, I have my share of complaints with them, too. I’m not being shill. I thought what I said to you was perfectly reasonable, but I feared you could misread it, thus my final sentence. If it took a minute or two for the email to arrive, and you find that unacceptable, I do think that’s an issue of managing expectations. But hey, we can disagree on that.

    I don’t see that being a terrible cost for the asserted benefits of the new system. Still, like others, I’m willing to wait and see how it shakes out.

    Did my second response, to Warwick, not feel more “responsive” to your concern? Why throw me under the bus, entirely? Goodness.

  • @charlie We plan to eliminate any lag in all queues thus eliminating the need for status on whether an email is queued or delivered. This is what we are working on.

  • @charlie. My point is that I’m not looking for patronizing direction from you about how I ought to feel about this upgrade or how I ought to respond to the immediate degradation in service that I experienced.

  • charlie arehart on June 16, 2011

    @Warwick, fair enough, and I suppose some readers may be regarding that as the perfect answer. But I’ll say that as you grow, it’s just reasonable (to me, from my own experience in web app server admin) that there may be delays. So while you may seek to eliminate it, it may just be a reality we will have to come to accept. But hey, if you can eliminate it, more power to you, and glad to see Chris and others happy. :-)

  • @warwick, thank you for your professional responses. I’m going to unsubscribe this thread. If the lag time problems continue in my next attempt at invoicing, I will move to a support ticket in order to avoid further cross-talk. Cheers.

  • charlie arehart on June 16, 2011

    @Chris, I was not intending to be patronizing. I was trying to help, and merely asked for clarification. I’m sorry you read it another way. You’ve gotten your answer from Harvest, and you’ve made clear your feeling of offense, and you now have my apology. I hope we can call a truce.

  • On June 15, Mal said,

    However, (using an iPad) if I reply – it wants to go back to notifications@ and this is the same on the iPhone too…
    Having done a reply (to test) I received a reply from Harvest saying that it’s an unmonitored mailbox blah blah…

    Has this been sorted out?

  • I’m glad you guys are working on this. I’d say for me its been a lot more than 1% that end up in the spam folder. I’ve actually taken to sending a PDF attachment in a separate email to ensure my clients were receiving the invoices. After waiting for months on a payment it was always awkward to have to ask… “did you get the invoice?”. Anyway, glad this is being addressed. Thanks!

  • I’m finding it hard to say something nice about this, or even just contain my frustration at how this can be considered as a “new and improved system.” I had already added { -all} to my DNS and have never had an issue, even if I did I would just send it to myself and then forward the email from my Google Apps accounts.

    Anyone who uses Google Apps or any email marketing application has to add a SPF record to their DNS, asking your customers to do the same isn’t a new idea nor an unreasonable request.

    This was one of your greatest features. Much like Brian J. I feel completely “small time” now, I’m invoicing from a random domain. I might as well be invoicing from

    I hope you reconsider alienating your customers that need this feature, I truly love harvest and have brought you many new clients, as I was singing your praises daily. If you do not signal that you intend n bringing this back, I will begin looking for an alternative that allows for this.

    Again I really love harvest and would hate to leave but this feature is a deal breaker for me.

  • Hi Sandy, we’re looking into the iPad issue – will let you know as soon as we figure it out.

  • Hi Joel, I’m sorry that you feel this way about the new email system!

    The new delivery system is a huge improvement for most of our customers – who are not technically inclined to deal with SPF records. It’s our goal to create a system that just works. The last thing we want is for our customers to have to worry and deal with technical details, just to make sure their emails are delivered.

    As for the “small time” concerns, the new Sender Profile feature is actually designed for address that. Many of the businesses that use Harvest have a department just to handle finance. But in Harvest, it used to be that you could send invoices from you (and your name would show up as the sender). With the new system, our customers can finally specify the department it’s from, and set the “reply-to” email to that department.

    Also, to repeat Doug’s point above, with most modern email clients, your clients should only see the display name (e.g. “IT Squad”) and they won’t be looking at the actual email address.

    Lastly, from our conversations with many customers, many of them actually prefer that invoice emails are sent from a 3rd party email address – especially when it’s an automated late invoice reminder message (as to avoid any awkwardness). As opposed to small time, many feel that it is actually more professional to have their billing handled by a professional business application such as Harvest.

  • Even though I understand that this change benefits the majority of your users, I am one of those users who has no difficulties in eding my domain’s DNS settings.

    I am very sorry that you chose not to provide the option that allowed me to send emails from my own domain. I have never had any issues with delivery of the emails and having to send emails from ‘’ is simply unacceptable for me.

    Unfortunately for me this means saying goodbye to harvest which is a pitty because I always enjoyed using this beautiful application.

  • Dudes, just have Harvest send the invoice to you, edit the email as a new message, and resend to client. It takes literally 5 seconds per invoice.

  • why email delivery notifications do not come from few domains?

  • I’m looking at taking on harvest after a few years with Freshbooks. How they handled their email was always an issue for me and I’m glad to see you have taken this issue seriously. The email getting there is far more important than domain name vanity.

    That being said there is a simple solution here that would suit everyone as far as I can see. We have used Postmarkapp for year managing our own customers emails. It allows us to configure SPF/DKIM easily on a customer by customer basis.

    For customers with more advanced needs, and the technical ability in the first place, why not either allow us to supply our own API key with postmark to use for delivering email? Obviously all issues with regards to delivery of the email then falls with the customer/Postmark rather than Harvest/Postmark. But as we would have reports from Postmark as to the status of the email delivery, I don’t see there being any issue there.

    Just an idea. We would still like to use our own domain but I’m not going to loose any sleep over it.


  • Hi @Nick

    Thanks for the suggestion! We thought long and hard about this option before we made any moves here. This isn’t something we plan for the near future, since we need to be a little more flexible in our email delivery options (we actually have had to move off Postmark for now) and troubleshooting customer API connection issues isn’t something we plan to undertake at this point.

    But email deliverability is really key to our service and we take it seriously. If you want to discuss in detail, please always feel free to contact me at

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