diff --git a/server/events/vcs/azuredevops_client.go b/server/events/vcs/azuredevops_client.go
index 40ab1fc8a2..c5b6b724cd 100644
--- a/server/events/vcs/azuredevops_client.go
+++ b/server/events/vcs/azuredevops_client.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"fmt"
 	"net/url"
+	"path/filepath"
 	"strings"
 	"time"
 
@@ -49,8 +50,8 @@ func NewAzureDevopsClient(hostname string, token string) (*AzureDevopsClient, er
 	return client, nil
 }
 
-// GetModifiedFiles returns the names of files that were modified in the merge request.
-// The names include the path to the file from the repo root, ex. parent/child/file.txt.
+// GetModifiedFiles returns the names of files that were modified in the merge request
+// relative to the repo root, e.g. parent/child/file.txt.
 func (g *AzureDevopsClient) GetModifiedFiles(repo models.Repo, pull models.PullRequest) ([]string, error) {
 	var files []string
 
@@ -66,13 +67,17 @@ func (g *AzureDevopsClient) GetModifiedFiles(repo models.Repo, pull models.PullR
 
 	for _, change := range r.Changes {
 		item := change.GetItem()
-		files = append(files, item.GetPath())
+		// Convert the path to a relative path from the repo's root.
+		relativePath := filepath.Clean("./" + item.GetPath())
+		files = append(files, relativePath)
 
 		// If the file was renamed, we'll want to run plan in the directory
 		// it was moved from as well.
 		changeType := azuredevops.Rename.String()
 		if change.ChangeType == &changeType {
-			files = append(files, change.GetSourceServerItem())
+			// Convert the path to a relative path from the repo's root.
+			relativePath = filepath.Clean("./" + change.GetSourceServerItem())
+			files = append(files, relativePath)
 		}
 	}
 
diff --git a/server/events/vcs/azuredevops_client_test.go b/server/events/vcs/azuredevops_client_test.go
index 1c91b0d650..8b6edb9267 100644
--- a/server/events/vcs/azuredevops_client_test.go
+++ b/server/events/vcs/azuredevops_client_test.go
@@ -203,7 +203,7 @@ func TestAzureDevopsClient_GetModifiedFiles(t *testing.T) {
 		"changeType": "add"
 	}
 ]}`
-	resp := fmt.Sprintf(itemRespTemplate, "file1.txt", "file1.txt", "file2.txt", "file2.txt")
+	resp := fmt.Sprintf(itemRespTemplate, "/file1.txt", "/file1.txt", "/file2.txt", "/file2.txt")
 	testServer := httptest.NewTLSServer(
 		http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 			switch r.RequestURI {
diff --git a/server/events/vcs/bitbucketcloud/client.go b/server/events/vcs/bitbucketcloud/client.go
index 3bb48b2cec..d55b7c598f 100644
--- a/server/events/vcs/bitbucketcloud/client.go
+++ b/server/events/vcs/bitbucketcloud/client.go
@@ -38,8 +38,8 @@ func NewClient(httpClient *http.Client, username string, password string, atlant
 	}
 }
 
-// GetModifiedFiles returns the names of files that were modified in the merge request.
-// The names include the path to the file from the repo root, ex. parent/child/file.txt.
+// GetModifiedFiles returns the names of files that were modified in the merge request
+// relative to the repo root, e.g. parent/child/file.txt.
 func (b *Client) GetModifiedFiles(repo models.Repo, pull models.PullRequest) ([]string, error) {
 	var files []string
 
diff --git a/server/events/vcs/bitbucketserver/client.go b/server/events/vcs/bitbucketserver/client.go
index 27796198e8..bff3b6258a 100644
--- a/server/events/vcs/bitbucketserver/client.go
+++ b/server/events/vcs/bitbucketserver/client.go
@@ -58,8 +58,8 @@ func NewClient(httpClient *http.Client, username string, password string, baseUR
 	}, nil
 }
 
-// GetModifiedFiles returns the names of files that were modified in the merge request.
-// The names include the path to the file from the repo root, ex. parent/child/file.txt.
+// GetModifiedFiles returns the names of files that were modified in the merge request
+// relative to the repo root, e.g. parent/child/file.txt.
 func (b *Client) GetModifiedFiles(repo models.Repo, pull models.PullRequest) ([]string, error) {
 	var files []string
 
diff --git a/server/events/vcs/client.go b/server/events/vcs/client.go
index 2b72fc2140..153af1265f 100644
--- a/server/events/vcs/client.go
+++ b/server/events/vcs/client.go
@@ -21,6 +21,8 @@ import (
 
 // Client is used to make API calls to a VCS host like GitHub or GitLab.
 type Client interface {
+	// GetModifiedFiles returns the names of files that were modified in the merge request
+	// relative to the repo root, e.g. parent/child/file.txt.
 	GetModifiedFiles(repo models.Repo, pull models.PullRequest) ([]string, error)
 	CreateComment(repo models.Repo, pullNum int, comment string) error
 	PullIsApproved(repo models.Repo, pull models.PullRequest) (bool, error)
diff --git a/server/events/vcs/github_client.go b/server/events/vcs/github_client.go
index 2f66699b24..11220b1958 100644
--- a/server/events/vcs/github_client.go
+++ b/server/events/vcs/github_client.go
@@ -61,8 +61,8 @@ func NewGithubClient(hostname string, user string, pass string) (*GithubClient,
 	}, nil
 }
 
-// GetModifiedFiles returns the names of files that were modified in the pull request.
-// The names include the path to the file from the repo root, ex. parent/child/file.txt.
+// GetModifiedFiles returns the names of files that were modified in the pull request
+// relative to the repo root, e.g. parent/child/file.txt.
 func (g *GithubClient) GetModifiedFiles(repo models.Repo, pull models.PullRequest) ([]string, error) {
 	var files []string
 	nextPage := 0
diff --git a/server/events/vcs/gitlab_client.go b/server/events/vcs/gitlab_client.go
index c96550adb3..002822805e 100644
--- a/server/events/vcs/gitlab_client.go
+++ b/server/events/vcs/gitlab_client.go
@@ -92,8 +92,8 @@ func NewGitlabClient(hostname string, token string, logger *logging.SimpleLogger
 	return client, nil
 }
 
-// GetModifiedFiles returns the names of files that were modified in the merge request.
-// The names include the path to the file from the repo root, ex. parent/child/file.txt.
+// GetModifiedFiles returns the names of files that were modified in the merge request
+// relative to the repo root, e.g. parent/child/file.txt.
 func (g *GitlabClient) GetModifiedFiles(repo models.Repo, pull models.PullRequest) ([]string, error) {
 	const maxPerPage = 100
 	var files []string
diff --git a/server/events/yaml/raw/project.go b/server/events/yaml/raw/project.go
index d30ee01474..e19fe6e5ca 100644
--- a/server/events/yaml/raw/project.go
+++ b/server/events/yaml/raw/project.go
@@ -67,10 +67,10 @@ func (p Project) Validate() error {
 
 func (p Project) ToValid() valid.Project {
 	var v valid.Project
-	cleanedDir := filepath.Clean(*p.Dir)
-	if cleanedDir == "/" {
-		cleanedDir = "."
-	}
+	// Prepend ./ and then run .Clean() so we're guaranteed to have a relative
+	// directory. This is necessary because we use this dir without sanitation
+	// in DefaultProjectFinder.
+	cleanedDir := filepath.Clean("./" + *p.Dir)
 	v.Dir = cleanedDir
 
 	if p.Workspace == nil || *p.Workspace == "" {
diff --git a/server/events/yaml/raw/project_test.go b/server/events/yaml/raw/project_test.go
index 8da75c01f4..626f09b54f 100644
--- a/server/events/yaml/raw/project_test.go
+++ b/server/events/yaml/raw/project_test.go
@@ -281,8 +281,9 @@ func TestProject_ToValid(t *testing.T) {
 				},
 			},
 		},
+		// Directories.
 		{
-			description: "dir with /",
+			description: "dir set to /",
 			input: raw.Project{
 				Dir: String("/"),
 			},
@@ -295,6 +296,20 @@ func TestProject_ToValid(t *testing.T) {
 				},
 			},
 		},
+		{
+			description: "dir starting with /",
+			input: raw.Project{
+				Dir: String("/a/b/c"),
+			},
+			exp: valid.Project{
+				Dir:       "a/b/c",
+				Workspace: "default",
+				Autoplan: valid.Autoplan{
+					WhenModified: []string{"**/*.tf*"},
+					Enabled:      true,
+				},
+			},
+		},
 		{
 			description: "dir with trailing slash",
 			input: raw.Project{
@@ -324,6 +339,49 @@ func TestProject_ToValid(t *testing.T) {
 				},
 			},
 		},
+		{
+			description: "dir set to ./",
+			input: raw.Project{
+				Dir: String("./"),
+			},
+			exp: valid.Project{
+				Dir:       ".",
+				Workspace: "default",
+				Autoplan: valid.Autoplan{
+					WhenModified: []string{"**/*.tf*"},
+					Enabled:      true,
+				},
+			},
+		},
+		{
+			description: "dir set to ././",
+			input: raw.Project{
+				Dir: String("././"),
+			},
+			exp: valid.Project{
+				Dir:       ".",
+				Workspace: "default",
+				Autoplan: valid.Autoplan{
+					WhenModified: []string{"**/*.tf*"},
+					Enabled:      true,
+				},
+			},
+		},
+		{
+			description: "dir set to .",
+			input: raw.Project{
+				Dir: String("."),
+			},
+			exp: valid.Project{
+				Dir:       ".",
+				Workspace: "default",
+				Autoplan: valid.Autoplan{
+					WhenModified: []string{"**/*.tf*"},
+					Enabled:      true,
+				},
+			},
+		},
+
 		{
 			description: "workspace set to empty string",
 			input: raw.Project{