diff --git a/api/client.go b/api/client.go
index f23edbc556..5654256ccb 100644
--- a/api/client.go
+++ b/api/client.go
@@ -228,35 +228,41 @@ func (c *Config) ConfigureTLS() error {
 //
 // This also removes any trailing "/v1"; we'll use that in our commands so we
 // don't require it from users.
-func (c *Config) setAddress(addr string) {
-	defer func() {
-		c.Address = strings.TrimSuffix(c.Address, "/")
-		c.Address = strings.TrimSuffix(c.Address, "/v1")
-	}()
-
-	split := strings.Split(strings.TrimSuffix("/", addr), "/")
-	if len(split) < 5 {
-		return
-	}
-
-	// ..../org/<org id>/project/<project id>
-	if split[len(split)-4] == "org" {
-		c.Org = split[len(split)-3]
-		if split[len(split)-2] == "project" {
-			c.Project = split[len(split)-1]
-		}
-		c.Address = strings.Join(split[0:len(split)-4], "/")
-		return
+func (c *Config) setAddress(addr string) error {
+	u, err := url.Parse(addr)
+	if err != nil {
+		return fmt.Errorf("error parsing address: %w", err)
 	}
+	c.Address = fmt.Sprintf("%s://%s", u.Scheme, u.Host)
 
-	// ..../org/<org id>/project/<project id>
-	if split[len(split)-2] == "org" {
-		c.Org = split[len(split)-1]
-		c.Address = strings.Join(split[0:len(split)-2], "/")
-		return
+	path := strings.TrimPrefix(u.Path, "/v1")
+	path = strings.TrimPrefix(path, "/")
+	if path == "" {
+		return nil
 	}
 
-	return
+	split := strings.Split(path, "/")
+	switch len(split) {
+	case 0:
+	case 2:
+		if split[0] != "org" {
+			return fmt.Errorf("expected org segment in address, found %q", split[0])
+		}
+		c.Org = split[1]
+	case 4:
+		if split[0] != "org" {
+			return fmt.Errorf("expected org segment in address, found %q", split[0])
+		}
+		c.Org = split[1]
+		if split[2] != "project" {
+			return fmt.Errorf("expected project segment in address, found %q", split[2])
+		}
+		c.Project = split[3]
+	default:
+		return fmt.Errorf("unexpected number of segments in address")
+	}
+
+	return nil
 }
 
 // ReadEnvironment reads configuration information from the environment. If
@@ -425,7 +431,9 @@ func NewClient(c *Config) (*Client, error) {
 		}
 	}
 
-	c.setAddress(c.Address)
+	if err := c.setAddress(c.Address); err != nil {
+		return nil, err
+	}
 
 	return &Client{
 		config: c,
@@ -435,11 +443,11 @@ func NewClient(c *Config) (*Client, error) {
 // Sets the address of Watchtower in the client. The format of address should
 // be "<Scheme>://<Host>:<Port>". Setting this on a client will override the
 // value of the WATCHTOWER_ADDR environment variable.
-func (c *Client) SetAddress(addr string) {
+func (c *Client) SetAddress(addr string) error {
 	c.modifyLock.Lock()
 	defer c.modifyLock.Unlock()
 
-	c.config.setAddress(addr)
+	return c.config.setAddress(addr)
 }
 
 // SetLimiter will set the rate limiter for this client.  This method is
@@ -638,7 +646,7 @@ func (c *Client) NewRequest(ctx context.Context, method, requestPath string, bod
 			User:   u.User,
 			Scheme: u.Scheme,
 			Host:   host,
-			Path:   path.Join(u.Path, requestPath, "v1", "org", org, "project", project),
+			Path:   path.Join(u.Path, "v1", "org", org, "project", project, requestPath),
 		},
 		Host: u.Host,
 	}
diff --git a/api/client_test.go b/api/client_test.go
new file mode 100644
index 0000000000..2d451c85b7
--- /dev/null
+++ b/api/client_test.go
@@ -0,0 +1,90 @@
+package api
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestConfigSetAddress(t *testing.T) {
+	type test struct {
+		name    string
+		input   string
+		address string
+		err     string
+		org     string
+		project string
+	}
+
+	tests := []test{
+		{
+			"bare",
+			"http://127.0.0.1:9200",
+			"http://127.0.0.1:9200",
+			"",
+			"",
+			"",
+		},
+		{
+			"bare with version",
+			"http://127.0.0.1:9200/v1",
+			"http://127.0.0.1:9200",
+			"",
+			"",
+			"",
+		},
+		{
+			"bare with version and trailing slash",
+			"http://127.0.0.1:9200/v1/",
+			"http://127.0.0.1:9200",
+			"",
+			"",
+			"",
+		},
+		{
+			"invalid org",
+			"http://127.0.0.1:9200/v1/org",
+			"http://127.0.0.1:9200",
+			"unexpected number of segments in address",
+			"",
+			"",
+		},
+		{
+			"valid org",
+			"http://127.0.0.1:9200/v1/org/orgid",
+			"http://127.0.0.1:9200",
+			"",
+			"orgid",
+			"",
+		},
+		{
+			"invalid project",
+			"http://127.0.0.1:9200/v1/org/orgid/project",
+			"http://127.0.0.1:9200",
+			"unexpected number of segments in address",
+			"",
+			"",
+		},
+		{
+			"valid project",
+			"http://127.0.0.1:9200/v1/org/orgid/project/projid",
+			"http://127.0.0.1:9200",
+			"",
+			"orgid",
+			"projid",
+		},
+	}
+
+	for _, v := range tests {
+		t.Run(v.name, func(t *testing.T) {
+			var c Config
+			err := c.setAddress(v.input)
+			if err != nil {
+				assert.Equal(t, v.err, err.Error())
+			}
+			assert.Equal(t, v.address, c.Address)
+			assert.Equal(t, v.org, c.Org)
+			assert.Equal(t, v.project, c.Project)
+		})
+	}
+}