Review of Gmail and Other Email Account Scheduling and Streamlining Tools

Welcome to My Personal Finance Journey! If you are new here, please read the “About” or “First-Time Visitor” pages to find out more about us. If you would like to receive free updates on articles like this by email, then sign up here or you can subscribe to the RSS feed. Also, check us out on Twitter or Facebook. Thanks for visiting! Keep on learning!

Back in June of 2012, I published an article comparing Google’s Gmail and Calendar features to Microsoft Outlook’s Calendar and email management capability.

After posting the article, I received a great comment from Robert of The College Investor saying that he really enjoys using Gmail, but wishes that a “Send at a Specific Time/Date” or “Send Later” feature came built in to Gmail as a default when you sign up.

Having remembered AOL having this feature back in the “stone-age” (a.k.a. the 90’s), I figured that SURELY some individual or company had thought of building an application or add-in to email applications that would provide this functionality.

In doing some searching around the Interwebs, I did find quite a few different applications that provided added email functionality (complete with Send it Later/Email Scheduling capability) to Gmail and other email providers.

Listed below is a summary of my findings of the different options available for people looking for email scheduling capability. 

Gmail Email Scheduling Applications

In today’s society, Gmail is arguably the most popular web email Internet provider. I know that myself and pretty much every other personal finance blogger around uses Gmail. Heck! Companies have even thrown in the towel in trying to create their own email applications and instead just have their email hosted with Google Apps. Not that I can blame them – Gmail is fast, simple, and free/very cheap!

Because of Gmail’s prevalence, it’s not surprising to find out that add-ins have been created specifically for Gmail to provide email scheduling and other capability.


From what I could tell, Streak is the only Gmail scheduling add-in that is currently totally free (as of September 2012). Generally, what seems to have happened is that all of these add-ins start off free during Beta testing, but once they gather enough subscribers/users, they start charging a monthly fee. Since Streak is still totally free, it is the Gmail scheduling tool I chose to install on my computer.

Streak offers a nice email scheduling tool that integrates right in to the “Compose an Email” window in Gmail (see screenshot below). To schedule an email, you simply click the “Send it Later” button and specify the date and time. The only critical remark I have of this scheduling program is that the time/date format is very specific, and you must follow their template suggestions to the letter.

For example, tomorrow at 8am would work fine for scheduling an email, but if you typed tomorrow, 8am (with a comma), it might not work! Just be careful here with the formatting, and you’ll be fine!

In addition to email scheduling, Streak also offers a very nice CRM folder system. Personally, I didn’t look in to this very much since I have a custom folder system that I use in Microsoft Outlook, but it might be worth exploring if you desire some more structure in your Gmail inbox.


In general, I would say that Boomerang is much more popular and well-established than Streak. However, this popularity also comes at the price of $5-$15 per month if you’d like to have unlimited email scheduling. But, Boomerang does have a free option which currently gives you only 10 message credits per month.

Nevertheless, Boomerang boasts some very useful email reminder and follow up features in addition to “Send it Later” capability. For example, I email back and forth with many people whom generally require multiple follow up emails to elicit a response. To handle this, I have an automatic reminder set up in my Outlook calendar that pops up once a week to follow up on emails in my “Waiting For” folder.

However, Boomerang does this automatically for you – directly from your Gmail Inbox. You simply click a button on the email window to specify the time and date that you’d like the email to be sent back to your Inbox so that you can follow up if you have or have not heard back yet.

Right Inbox

The next Gmail scheduling add-in that I came across in my search was Right Inbox. From what I could tell, not only is Right Inbox cheaper than Boomerang ($5 per month or $40 per year), but it also has all of the features that Boomerang boasts and then a few others!

As with Boomerang, you can schedule emails to be sent at a specific time and date and also mark email to be returned to your email inbox for follow up later if someone or no one responds. In addition, you get email tracking functionality, which allows you to be notified if an email is opened and even shows you which links within an email are clicked! This is pretty cool if you ask me! 🙂

Other Email Account Scheduling Tools

Microsoft Outlook

Interestingly enough, Microsoft Outlook features a fairly good email scheduling tool already built in to it! To access this option, simply open up a new email, click the “Options” menu, then “Delay Delivery,” and then select the time and date that you want Outlook to wait to send the message until. Please see the screenshot below for an example of how to do this. This link also gives a nice description of this process as well. 
Side note: You can easily integrate your normal Gmail email account in to the Outlook program. I did this about 2 years ago, and it has VERY much streamlined and organized my life! 
The only thing I don’t like about Outlook’s built-in email scheduling tool is that your computer has to be ON/working and Outlook placed in the “online” state in order for your messages to actually be sent at the time you specified. 
In other words, unlike Gmail scheduling which runs all of the time on Google’s remote servers, your scheduled emails in Outlook are stored on your local computer only until the “send” is completed. This means that your email won’t be sent if your computer falls asleep, you shut down your computer for the night, or you simply work on Outlook in the “offline” state like I do all of the time in order to minimize distractions from incoming emails. 

In addition to this existing Outlook scheduling capability, Boomerang also has come up with an Outlook integration version of their email reminder tool. The cost of this is a one time fee of $30, but there is a 30 day free trial available!


Good ole’ AOL uh?! It seems like it has been around forever – because of course, it has! Right under our noses, AOL has featured a “Send it Later” feature for MANY years!

To access/use this feature (completely free mind you), simply create a free account, and then download the latest free AOL desktop software. Once you sign in (remember the sound of the old dial-up modems when we signed in in the late 90’s?), click the “Write Mail” button and then find the “Send Later” button on the “Compose Message” screen that pops up (see screenshot below).

After clicking the “Send Later” button, you then click the “Auto AOL” button in order to decide when things are sent and received.

How about you all? What provider/program do you use for email? Are you pretty satisfied with the system that it offers? If there was one thing you would change about it, what would it be?

Share your experiences by commenting below!

About the Author Jacob A Irwin

Hi folks! My name is Jacob. I am the owner and operator of My Personal Finance Journey. I started this blog in January of 2010 and have enjoyed the journey ever since. Since finishing up graduate school in Virginia in 2014, I have been working in biopharmaceutical development in Colorado. You can read more about me and this site here​. Please contact me if you have any questions!

follow me on:

Leave a Comment:

Shannon-ReadyForZero says September 7, 2012

I love Microsoft Outlook although I can’t use it on my laptop because I don’t have the Microsoft package. Because of this I’ve been using Boomerang to help out and generally find it very useful. Great article – it’s nice to have all the different options spelled out so nicely!

    MyPerFinJourney says October 22, 2012

    Glad to hear Boomerang works pretty well. What pricing package do you use with them?
    My recent post The Pros and Cons of a Down Payment Assistance Program

      Shannon-ReadyForZero says October 25, 2012

      I've actually been able to do the free package so far, but if I keep using it a lot I'll probably have to go up to the next price.
      My recent post What Should You Do Before Buying a House?

Ferdinand says September 8, 2012

Since i learned about Gmail, i have relied on it with everything about my emails. Its such a great tool with a lot of online/offline functionality.
My recent post A guide to cheaper mobile roaming

    MyPerFinJourney says October 22, 2012

    Glad you like Gmail Ferdinand! Is there anything about Gmail that you wish were changed?
    My recent post The Pros and Cons of a Down Payment Assistance Program

Add Your Reply