diff --git a/cmd/server.go b/cmd/server.go
index 5e2ded05bf..727cf2b49d 100644
--- a/cmd/server.go
+++ b/cmd/server.go
@@ -3,6 +3,7 @@ package cmd
 import (
 	"fmt"
 	"os"
+	"path/filepath"
 	"strings"
 
 	"github.com/atlantisnorth/atlantis/server"
@@ -293,15 +294,25 @@ func (s *ServerCmd) setAtlantisURL(config *server.Config) error {
 
 // setDataDir checks if ~ was used in data-dir and converts it to the actual
 // home directory. If we don't do this, we'll create a directory called "~"
-// instead of actually using home.
+// instead of actually using home. It also converts relative paths to absolute.
 func (s *ServerCmd) setDataDir(config *server.Config) error {
-	if strings.HasPrefix(config.DataDir, "~/") {
-		expanded, err := homedir.Expand(config.DataDir)
+	finalPath := config.DataDir
+
+	// Convert ~ to the actual home dir.
+	if strings.HasPrefix(finalPath, "~/") {
+		var err error
+		finalPath, err = homedir.Expand(finalPath)
 		if err != nil {
 			return errors.Wrap(err, "determining home directory")
 		}
-		config.DataDir = expanded
 	}
+
+	// Convert relative paths to absolute.
+	finalPath, err := filepath.Abs(finalPath)
+	if err != nil {
+		return errors.Wrap(err, "making data-dir absolute")
+	}
+	config.DataDir = finalPath
 	return nil
 }
 
diff --git a/cmd/server_test.go b/cmd/server_test.go
index cd5ac0ad4b..1045ff262e 100644
--- a/cmd/server_test.go
+++ b/cmd/server_test.go
@@ -3,6 +3,7 @@ package cmd_test
 import (
 	"io/ioutil"
 	"os"
+	"path/filepath"
 	"strings"
 	"testing"
 
@@ -283,8 +284,8 @@ func TestExecute_Defaults(t *testing.T) {
 	Equals(t, 4141, passedConfig.Port)
 }
 
-func TestExecute_ExpandHomeDir(t *testing.T) {
-	t.Log("Should expand the ~ in the home dir to the actual home dir.")
+func TestExecute_ExpandHomeInDataDir(t *testing.T) {
+	t.Log("If ~ is used as a data-dir path, should expand to absolute home path")
 	c := setup(map[string]interface{}{
 		cmd.GHUserFlag:  "user",
 		cmd.GHTokenFlag: "token",
@@ -298,6 +299,23 @@ func TestExecute_ExpandHomeDir(t *testing.T) {
 	Equals(t, home+"/this/is/a/path", passedConfig.DataDir)
 }
 
+func TestExecute_RelativeDataDir(t *testing.T) {
+	t.Log("Should convert relative dir to absolute.")
+	c := setup(map[string]interface{}{
+		cmd.GHUserFlag:  "user",
+		cmd.GHTokenFlag: "token",
+		cmd.DataDirFlag: "../",
+	})
+
+	// Figure out what ../ should be as an absolute path.
+	expectedAbsolutePath, err := filepath.Abs("../")
+	Ok(t, err)
+
+	err = c.Execute()
+	Ok(t, err)
+	Equals(t, expectedAbsolutePath, passedConfig.DataDir)
+}
+
 func TestExecute_GithubUser(t *testing.T) {
 	t.Log("Should remove the @ from the github username if it's passed.")
 	c := setup(map[string]interface{}{
@@ -326,7 +344,7 @@ func TestExecute_Flags(t *testing.T) {
 	t.Log("Should use all flags that are set.")
 	c := setup(map[string]interface{}{
 		cmd.AtlantisURLFlag:     "url",
-		cmd.DataDirFlag:         "path",
+		cmd.DataDirFlag:         "/path",
 		cmd.GHHostnameFlag:      "ghhostname",
 		cmd.GHUserFlag:          "user",
 		cmd.GHTokenFlag:         "token",
@@ -343,7 +361,7 @@ func TestExecute_Flags(t *testing.T) {
 	Ok(t, err)
 
 	Equals(t, "url", passedConfig.AtlantisURL)
-	Equals(t, "path", passedConfig.DataDir)
+	Equals(t, "/path", passedConfig.DataDir)
 	Equals(t, "ghhostname", passedConfig.GithubHostname)
 	Equals(t, "user", passedConfig.GithubUser)
 	Equals(t, "token", passedConfig.GithubToken)
@@ -361,7 +379,7 @@ func TestExecute_ConfigFile(t *testing.T) {
 	t.Log("Should use all the values from the config file.")
 	tmpFile := tempFile(t, `---
 atlantis-url: "url"
-data-dir: "path"
+data-dir: "/path"
 gh-hostname: "ghhostname"
 gh-user: "user"
 gh-token: "token"
@@ -381,7 +399,7 @@ require-approval: true`)
 	err := c.Execute()
 	Ok(t, err)
 	Equals(t, "url", passedConfig.AtlantisURL)
-	Equals(t, "path", passedConfig.DataDir)
+	Equals(t, "/path", passedConfig.DataDir)
 	Equals(t, "ghhostname", passedConfig.GithubHostname)
 	Equals(t, "user", passedConfig.GithubUser)
 	Equals(t, "token", passedConfig.GithubToken)