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I have this little desire (obsession) to find ways to use the Kindle for everything that I am reading. This includes PDF and other documents. Here are the ways I found to quickly transfer files.

Sending a PDF file to Kindle can be done by installing the Send to Kindle app from Amazon. Another way is by emailing the file to your personal Kindle email, or by attaching your Kindle via USB. You can also convert the PDF to the native Kindle format to use many of the eReader's features.

Read on to learn more about these different methods, including various alternatives.

Here's a sample PDF sent to the Kindle.

Exhibit A. Question from the PDF above:
In The Adventures of Tom Sawyer, Mark Twain wrote of a great law of human action. Tom discovered this after convincing other boys to do his task of whitewashing a fence for him. What was that law of human action?
Click here for multiple choices.

Send to Kindle app for PC or Mac

Amazon offers this tool for desktop computers. It is quick to install, easy to use, and well maintained.

Step 1 - Download and install

Go to the link below and download the program for your operating system:
https://www.amazon.com/gp/sendtokindle

For Linux computers, there is no corresponding app yet, but there are some alternatives we will cover later.

Step 2 - Sign in to Amazon

After installation, the app will open and you will be asked to sign-in with your Amazon account.

Then, a new item will appear in your right-click menu.

Step 3 - Send the files

Right click on a file and select this new "Send to Kindle" menu. A new window will open.

You will have options to select which device to deliver the file to, and to update the title and author name of the document.

You also have the option to convert the file into the native Kindle format to make it easier to read. More on this shortly.

You can also select multiple files and right click on them to send at the same time.

Step 4 - Sync your Kindle

Click send to begin the transfer.

Within a few minutes, you should see the document appear on your Kindle eReader automatically. You can also trigger a manual sync of the eReader by tapping on Settings > Sync Your Kindle.

Alternatives to Step 3

Instead of using the right click option, you can open the Send to Kindle app and drag files to it.

After dragging the files, you will see the same window in the previous step.

If this app doesn't automatically show up in Window's start menu, you can create a shortcut to the actual program by going to the installation folder using Windows explorer. By default the program location is:

C:\Program Files (x86)\Amazon\SendToKindle\SendToKindle.exe

Yet another option is to use the Send to Kindle printer driver that was installed alongside the program. To use this, click on Print on any Windows application and change the printer to "Send to Kindle".


Send to Kindle using email

Sending to Kindle using the email method works well across any platform or device. There's a bit of a onetime setup involved, but it shouldn't take you more than a few minutes to complete the whole process.

Step 1 - Find your personal Kindle email

Each Kindle device and Kindle app will have its own automatically generated email address. Let's call it the "Destination" email. This is where we will send the documents. The document will then be delivered wirelessly to the corresponding device or app within a few minutes.

There are multiple ways to find this email.

Using the Kindle eReader:
Go to Settings > All Settings > Your Account > Send-to-Kindle Email

Using the Kindle App:
Go to More > Settings > Send-to-Kindle email address

Using the Amazon's website:
Go to your Amazon account's Manage Content and Devices page.
Here's a shortcut: https://www.amazon.com/mycd

Next, go to Preferences, scroll down and click on Personal Document Settings.

Note the email address displayed. You can also change those email addresses by clicking on Edit.

So you don't have to dig up this email address again in the future, you can also save it as a contact in your favorite email tool, i.e. "My Kindle Paperwhite".

Step 2 - Add authorized sender

To prevent spam, Kindle will only accept documents from a pre-approved list of email addresses.

While still in the Personal Document Settings section of the Amazon website, scroll down to Approved Personal Document E-mail List.

Here you must add the email address that you will be using as your "From" email. It could be any email that you have access to. Note that this would be different from the email you noted in Step 1.

Step 3 - Send email with attachment

Next, open your "From" email inbox, and compose a new message. Fill-out the following fields:

TO: The "Destination" email you noted in Step 1.
FROM: The email you added in Step 2.
SUBJECT (optional): Can be empty.
BODY (optional): Can be empty.
ATTACHMENT: Attach the file you want to send. Pay attention to the filename as that is what Kindle will use as the title of the document.

Hit send and in a few moments you should see the file in your Kindle eReader.

Step 4 - Sync your Kindle

You can also trigger a manual sync by tapping Settings > Sync Your Kindle.

If you still don't see the file, check your email inbox for any messages. You will be notified if there is a problem with the attachment or you need to do additional steps.

Converting the PDF file format

PDF files might not be the easiest to read in the Kindle given the smaller screen. You can compensate for this somewhat by adjusting the layout to landscape.

You can also make reading easier by converting the PDF file to Kindle's native file format. This would enable, among other things:

  • Adjustments to font height and weight (bold).
  • Layout settings such as line spacing and margins.
  • Include this document in searching for text across all books (from the home screen).
  • Sync notes and highlights with other devices.
  • Sync page location with other devices.

Converting the file can be done by checking the option Convert PDF documents to Kindle format in the Send to Kindle app.

And if you are using the email approach, you just need to set the email's subject to "convert" (instead of an empty subject).

There is a trade-off though, with converting PDF files. You will lose all the formatting of the original file, including layout and placement of photos, tables, etc.

If you want to retain the ability to see both versions, a workaround is to send both the original PDF and the converted version. In your Kindle, they will then show up with different icons. The one that looks like an "A" are for PDFs and the file icon are for converted documents.


Upload to Kindle via USB

Another option to transfer files to the Kindle is by directly connecting the eReader to your computer with a USB cable.

The Kindle will turn into "USB Drive Mode" and allow you to access the contents using a regular file explorer.

Copy the files anywhere inside the "Documents" folder. Feel free to create a sub-folder if you wish, i.e. "Uploads". Kindle will read it just the same.

Once copying is done, safely remove and eject the Kindle from the computer. The Kindle will go back to normal mode and might take a few seconds to index the new files added. Afterwards, you will see the files on the home screen.

If you find yourself using this method often, it would be helpful to use a USB hub that has a power on and off switch. This would cut down the time of physically pulling the USB chord in and out of the devices.

Send to Kindle from Google Drive or Dropbox automatically

If you are already using cloud storage such as Google Drive or Dropbox, adding just a few steps can automate sending to the Kindle as well. This system can organize and backup your files, and upload them to the Kindle at the same time.

To begin, you would need a Zapier.com account. This tool will connect your cloud storage provider with an emailing tool. It will then send to the Kindle using the approach we discussed above.

Zapier will monitor new files saved to your cloud drive and fire off an email to your Kindle.

For this example, we will use Google Drive for cloud storage, and GMail for sending.

Preparation - Create folders in Google Drive

Go to Google Drive and create the folders that will host the files you want to send to Kindle.

I recommend two folders, one folder will send the file as is, and the other will convert the file to the Kindle's native format.

Go ahead and upload a PDF file into both folders.

Step 1 - Create a new Zap and Connect Google Drive

Login to Zapier and hit the large "Make a Zap" button on the upper left menu bar. A Zap is the term they use for each workflow that you setup. Rename the Zap to something descriptive such as "Send to Kindle".

You will be asked to select the "Trigger" that Zapier will monitor for changes. Select Google Drive.

For the "Trigger Event", select "New File in Folder".

Next you will be asked to select and authenticate the Google Drive account.

After that, for the "Setup Trigger", enter the folder you created in the previous step.

Conclude this step by clicking on "Test Trigger". You should see a success message saying that Zapier found a file.

Step 2 - Connect GMail

Next, we need to indicate what action will be performed. Select "GMail" as the app for this action.

For "Action Event", choose "Send Email". Then hit continue.

Then you will be asked to select and authenticate the GMail account to be used in sending the email.

Next, Set up the action as follows, all other fields can be left blank.

TO: Enter your personal Kindle Email (See here how to find this).
FROM: Your "From" email. This must be included in the Approved Personal Document E-mail List (discussed here).
SUBJECT: Kindle doesn't require this, but Zapier does. Just type any text such as "Send to Kindle", or use the File's Title.
BODY: Same as Subject.
ATTACHMENTS: Click on the field, and select "1.File". This represents the file that Zapier found in Step 1.

Finally, hit Test and you should be greeted with an encouraging confirmation message.

Your Zap is now ready. Click "Turn on Zap" and start uploading files to your Google drive. You should see them appear on your Kindle momentarily.

Step 3 - Sync your Kindle

You can also trigger the Kindle's manual sync to speed up the process.

The free account for Zapier is limited to running every 15 minutes. But you can trigger a manual run by clicking "Run Zap" in the Zapier dashboard. There is also a 1000 task run limit per month.

Step 4 - Setup convert folder (optional)

If you want to convert the files sent to the Kindle, you would need to create a new Zap with almost identical settings as the one you just created. The differences would be on:

Setup Trigger: Select a different folder in Google Drive. All files dragged here will be sent in a converted format.

Send Email > Subject: This should be the word "convert"

Save and Turn On the new zap to start monitoring the 2nd Google Drive folder.

With this system you can organize and backup PDF files in Google Drive and automatically send them to Kindle. This is very handy if you have a lot of files that you want to transfer and on frequent times during the day.

I also find this as a good alternative for Linux computers and Chromebooks who don't have the Amazon Send to Kindle app available.

Other information

  • Here's a more complete list of file types that you can send to the Kindle:
    PDF (.PDF)
    Microsoft Word (.DOC, .DOCX)
    HTML (.HTML, .HTM)
    RTF (.RTF)
    JPEG (.JPEG, .JPG)
    Kindle Format (.MOBI, .AZW)
    GIF (.GIF)
    PNG (.PNG)
    BMP (.BMP)
  • Some Kindle devices can receive documents over the mobile network (3G/4G). For these services, Amazon may charge a fee for delivering documents over mobile. Check "Personal Document Settings" and "Whispersync Settings" to make sure if your device has this service enabled.
  • If your Kindle does have 3G/4G network connectivity, another way to avoid the fees is to use "@free.kindle.com". Use this as the domain name of your "Destination" email, instead of "@kindle.com".

These are the ways to send PDF and other files to the Kindle. Do you know of other methods? Or do you have a Kindle or eReader question you need investigated? Please don't hesitate to drop us a line.

P.S.
Here's the answer to the Exhibit A puzzle above:

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