diff --git a/keys/README.md b/keys/README.md
index c900682a0..de81d83bf 100644
--- a/keys/README.md
+++ b/keys/README.md
@@ -1,9 +1,22 @@
-# Insecure Keypair
+# Insecure Keypairs
 
 These keys are the "insecure" public/private keypair we offer to
 [base box creators](https://www.vagrantup.com/docs/boxes/base.html) for use in their base boxes so that
 vagrant installations can automatically SSH into the boxes.
 
+# Vagrant Keypairs
+
+There are currently two "insecure" public/private keypairs for 
+Vagrant. One keypair was generated using the older RSA algorithm
+and the other keypair was generated using the more recent ED25519
+algorithm. 
+
+The `vagrant.pub` file includes the public key for both keypairs. It 
+is important for box creators to include both keypairs as versions of 
+Vagrant prior to 2.3.8 will only use the RSA private key.
+
+# Custom Keys
+
 If you're working with a team or company or with a custom box and
 you want more secure SSH, you should create your own keypair
 and configure the private key in the Vagrantfile with
diff --git a/keys/vagrant.key.ed25519 b/keys/vagrant.key.ed25519
new file mode 100644
index 000000000..73d365e7f
--- /dev/null
+++ b/keys/vagrant.key.ed25519
@@ -0,0 +1,7 @@
+-----BEGIN OPENSSH PRIVATE KEY-----
+b3BlbnNzaC1rZXktdjEAAAAABG5vbmUAAAAEbm9uZQAAAAAAAAABAAAAMwAAAAtzc2gtZW
+QyNTUxOQAAACDdWHcQaTZc8Q6nycsP0CqMNRfsLxvYVxqKosrHyTp+WAAAAJj2TBMT9kwT
+EwAAAAtzc2gtZWQyNTUxOQAAACDdWHcQaTZc8Q6nycsP0CqMNRfsLxvYVxqKosrHyTp+WA
+AAAEAveRHRHSCjIxbNKHDRzezD0U3R3UEEmS7R33fzvPQAD91YdxBpNlzxDqfJyw/QKow1
+F+wvG9hXGoqiysfJOn5YAAAAEHNwb3hAdmFncmFudC1kZXYBAgMEBQ==
+-----END OPENSSH PRIVATE KEY-----
diff --git a/keys/vagrant.key.rsa b/keys/vagrant.key.rsa
new file mode 100644
index 000000000..7d6a08390
--- /dev/null
+++ b/keys/vagrant.key.rsa
@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEogIBAAKCAQEA6NF8iallvQVp22WDkTkyrtvp9eWW6A8YVr+kz4TjGYe7gHzI
+w+niNltGEFHzD8+v1I2YJ6oXevct1YeS0o9HZyN1Q9qgCgzUFtdOKLv6IedplqoP
+kcmF0aYet2PkEDo3MlTBckFXPITAMzF8dJSIFo9D8HfdOV0IAdx4O7PtixWKn5y2
+hMNG0zQPyUecp4pzC6kivAIhyfHilFR61RGL+GPXQ2MWZWFYbAGjyiYJnAmCP3NO
+Td0jMZEnDkbUvxhMmBYSdETk1rRgm+R4LOzFUGaHqHDLKLX+FIPKcF96hrucXzcW
+yLbIbEgE98OHlnVYCzRdK8jlqm8tehUc9c9WhQIBIwKCAQEA4iqWPJXtzZA68mKd
+ELs4jJsdyky+ewdZeNds5tjcnHU5zUYE25K+ffJED9qUWICcLZDc81TGWjHyAqD1
+Bw7XpgUwFgeUJwUlzQurAv+/ySnxiwuaGJfhFM1CaQHzfXphgVml+fZUvnJUTvzf
+TK2Lg6EdbUE9TarUlBf/xPfuEhMSlIE5keb/Zz3/LUlRg8yDqz5w+QWVJ4utnKnK
+iqwZN0mwpwU7YSyJhlT4YV1F3n4YjLswM5wJs2oqm0jssQu/BT0tyEXNDYBLEF4A
+sClaWuSJ2kjq7KhrrYXzagqhnSei9ODYFShJu8UWVec3Ihb5ZXlzO6vdNQ1J9Xsf
+4m+2ywKBgQD6qFxx/Rv9CNN96l/4rb14HKirC2o/orApiHmHDsURs5rUKDx0f9iP
+cXN7S1uePXuJRK/5hsubaOCx3Owd2u9gD6Oq0CsMkE4CUSiJcYrMANtx54cGH7Rk
+EjFZxK8xAv1ldELEyxrFqkbE4BKd8QOt414qjvTGyAK+OLD3M2QdCQKBgQDtx8pN
+CAxR7yhHbIWT1AH66+XWN8bXq7l3RO/ukeaci98JfkbkxURZhtxV/HHuvUhnPLdX
+3TwygPBYZFNo4pzVEhzWoTtnEtrFueKxyc3+LjZpuo+mBlQ6ORtfgkr9gBVphXZG
+YEzkCD3lVdl8L4cw9BVpKrJCs1c5taGjDgdInQKBgHm/fVvv96bJxc9x1tffXAcj
+3OVdUN0UgXNCSaf/3A/phbeBQe9xS+3mpc4r6qvx+iy69mNBeNZ0xOitIjpjBo2+
+dBEjSBwLk5q5tJqHmy/jKMJL4n9ROlx93XS+njxgibTvU6Fp9w+NOFD/HvxB3Tcz
+6+jJF85D5BNAG3DBMKBjAoGBAOAxZvgsKN+JuENXsST7F89Tck2iTcQIT8g5rwWC
+P9Vt74yboe2kDT531w8+egz7nAmRBKNM751U/95P9t88EDacDI/Z2OwnuFQHCPDF
+llYOUI+SpLJ6/vURRbHSnnn8a/XG+nzedGH5JGqEJNQsz+xT2axM0/W/CRknmGaJ
+kda/AoGANWrLCz708y7VYgAtW2Uf1DPOIYMdvo6fxIB5i9ZfISgcJ/bbCUkFrhoH
++vq/5CIWxCPp0f85R4qxxQ5ihxJ0YDQT9Jpx4TMss4PSavPaBH3RXow5Ohe+bYoQ
+NE5OgEXk2wVfZczCZpigBKbKZHNYcelXtTt/nP3rsCuGcM4h53s=
+-----END RSA PRIVATE KEY-----
diff --git a/keys/vagrant.pub b/keys/vagrant.pub
index 18a9c00fd..78a8ccf51 100644
--- a/keys/vagrant.pub
+++ b/keys/vagrant.pub
@@ -1 +1,2 @@
 ssh-rsa AAAAB3NzaC1yc2EAAAABIwAAAQEA6NF8iallvQVp22WDkTkyrtvp9eWW6A8YVr+kz4TjGYe7gHzIw+niNltGEFHzD8+v1I2YJ6oXevct1YeS0o9HZyN1Q9qgCgzUFtdOKLv6IedplqoPkcmF0aYet2PkEDo3MlTBckFXPITAMzF8dJSIFo9D8HfdOV0IAdx4O7PtixWKn5y2hMNG0zQPyUecp4pzC6kivAIhyfHilFR61RGL+GPXQ2MWZWFYbAGjyiYJnAmCP3NOTd0jMZEnDkbUvxhMmBYSdETk1rRgm+R4LOzFUGaHqHDLKLX+FIPKcF96hrucXzcWyLbIbEgE98OHlnVYCzRdK8jlqm8tehUc9c9WhQ== vagrant insecure public key
+ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIN1YdxBpNlzxDqfJyw/QKow1F+wvG9hXGoqiysfJOn5Y vagrant insecure public key
diff --git a/keys/vagrant.pub.ed25519 b/keys/vagrant.pub.ed25519
new file mode 100644
index 000000000..ef65a946c
--- /dev/null
+++ b/keys/vagrant.pub.ed25519
@@ -0,0 +1 @@
+ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIN1YdxBpNlzxDqfJyw/QKow1F+wvG9hXGoqiysfJOn5Y vagrant insecure public key
diff --git a/keys/vagrant.pub.rsa b/keys/vagrant.pub.rsa
new file mode 100644
index 000000000..18a9c00fd
--- /dev/null
+++ b/keys/vagrant.pub.rsa
@@ -0,0 +1 @@
+ssh-rsa AAAAB3NzaC1yc2EAAAABIwAAAQEA6NF8iallvQVp22WDkTkyrtvp9eWW6A8YVr+kz4TjGYe7gHzIw+niNltGEFHzD8+v1I2YJ6oXevct1YeS0o9HZyN1Q9qgCgzUFtdOKLv6IedplqoPkcmF0aYet2PkEDo3MlTBckFXPITAMzF8dJSIFo9D8HfdOV0IAdx4O7PtixWKn5y2hMNG0zQPyUecp4pzC6kivAIhyfHilFR61RGL+GPXQ2MWZWFYbAGjyiYJnAmCP3NOTd0jMZEnDkbUvxhMmBYSdETk1rRgm+R4LOzFUGaHqHDLKLX+FIPKcF96hrucXzcWyLbIbEgE98OHlnVYCzRdK8jlqm8tehUc9c9WhQ== vagrant insecure public key