diff --git a/pkg/api/dialer.go b/pkg/api/dialer.go
new file mode 100644
index 00000000..f146597a
--- /dev/null
+++ b/pkg/api/dialer.go
@@ -0,0 +1,100 @@
+package api
+
+import (
+	"context"
+	"errors"
+	"net"
+	"os"
+	"strings"
+	"testing"
+	"time"
+)
+
+// DialContextFunc is a function that dials a context, network, and address.
+type DialContextFunc func(ctx context.Context, network, address string) (net.Conn, error)
+
+// RetryDialUntilSuccess will retry every `retryTimeout` until it succeeds.
+func RetryDialUntilSuccess(retryTimeout time.Duration) DialContextFunc {
+	return func(ctx context.Context, network, address string) (net.Conn, error) {
+		for {
+			dialer := &net.Dialer{
+				Timeout:   retryTimeout,
+				KeepAlive: 30 * time.Second, // Similar to the default HTTP dialer.
+			}
+			c, err := dialer.DialContext(ctx, network, address)
+			if err != nil {
+				if errors.Is(err, context.DeadlineExceeded) {
+					continue
+				}
+				if errors.Is(err, os.ErrDeadlineExceeded) {
+					continue
+				}
+				// Testing hook.
+				if testing.Testing() && strings.Contains(err.Error(), "connection refused") {
+					continue
+				}
+			}
+			return c, err
+		}
+	}
+}
+
+// DialNoTimeout will block with no timeout or until the context is canceled.
+func DialNoTimeout() DialContextFunc {
+	dialer := &net.Dialer{}
+	return dialer.DialContext
+}
+
+// DefaultHTTPDialer has the same options as the default HTTP dialer.
+func DefaultHTTPDialer() DialContextFunc {
+	dialer := &net.Dialer{
+		Timeout:   30 * time.Second,
+		KeepAlive: 30 * time.Second,
+	}
+	return dialer.DialContext
+}
+
+// RacingDialer is a custom dialer that attempts to connect to a given address.
+//
+// It uses two different dialers.
+// The dialer connects first is returned, and the other is canceled.
+//
+// The first has a short timeout (200 ms) and continues to retry until it succeeds.
+// The second dialer has no timeout and will block until it either succeeds or fails.
+//
+// We are doing this because we see connection timeouts perhaps caused by some competing network routes.
+// Our workaround is to use a short timeout dialer that will retry until it succeeds.
+func RacingDialer(dialers ...DialContextFunc) DialContextFunc {
+	if len(dialers) == 0 {
+		return DialNoTimeout()
+	}
+
+	return func(ctx context.Context, network, address string) (net.Conn, error) {
+		ctx, cancel := context.WithCancel(ctx)
+		defer cancel()
+
+		type dialResult struct {
+			conn net.Conn
+			err  error
+		}
+		resultCh := make(chan dialResult, len(dialers))
+		for _, dialer := range dialers {
+			go func(d DialContextFunc) {
+				c, err := d(ctx, network, address)
+				resultCh <- dialResult{conn: c, err: err}
+			}(dialer)
+		}
+
+		var connError error
+		for range len(dialers) {
+			res := <-resultCh
+			if res.err == nil {
+				cancel()
+				return res.conn, nil
+			} else {
+				connError = res.err
+			}
+		}
+		return nil, connError
+	}
+}
diff --git a/pkg/api/dialer_test.go b/pkg/api/dialer_test.go
new file mode 100644
index 00000000..ae64383c
--- /dev/null
+++ b/pkg/api/dialer_test.go
@@ -0,0 +1,98 @@
+package api
+
+import (
+	"context"
+	"fmt"
+	"net"
+	"sync"
+	"testing"
+	"time"
+)
+
+func TestRetryDialUntilSuccess(t *testing.T) {
+	// "reserve" a port.
+	ln, err := net.Listen("tcp", ":0")
+	if err != nil {
+		t.Fatalf("failed to listen on random port: %v", err)
+	}
+	port := ln.Addr().(*net.TCPAddr).Port
+	_ = ln.Close()
+
+	ctx, cancel := context.WithCancel(t.Context())
+	defer cancel()
+
+	var wg sync.WaitGroup
+	wg.Add(1)
+	go func() {
+		defer wg.Done()
+		// Wait a a bit so that the dialer will retry a few times.
+		time.Sleep(50 * time.Millisecond)
+
+		// Start a server to listen on the reserved port.
+		listener, err := net.Listen("tcp", fmt.Sprintf(":%d", port))
+		if err != nil {
+			cancel()
+			return
+		}
+		t.Log("listener", listener.Addr())
+		defer listener.Close()
+		conn, err := listener.Accept()
+		if err != nil {
+			cancel()
+			return
+		}
+		defer conn.Close()
+	}()
+
+	dialer := RetryDialUntilSuccess(10 * time.Millisecond)
+	conn, err := dialer(ctx, "tcp", fmt.Sprintf("localhost:%d", port))
+	if err != nil {
+		t.Fatalf("failed to dial: %v", err)
+	}
+	conn.Close()
+	wg.Wait()
+}
+
+func TestRacingDialer(t *testing.T) {
+	// "reserve" a port.
+	ln, err := net.Listen("tcp", ":0")
+	if err != nil {
+		t.Fatalf("failed to listen on random port: %v", err)
+	}
+	port := ln.Addr().(*net.TCPAddr).Port
+	_ = ln.Close()
+
+	ctx, cancel := context.WithCancel(t.Context())
+	defer cancel()
+
+	var wg sync.WaitGroup
+	wg.Add(1)
+	go func() {
+		defer wg.Done()
+		// Wait a a bit so that the dialer will retry a few times.
+		time.Sleep(50 * time.Millisecond)
+
+		// Start a server to listen on the reserved port.
+		listener, err := net.Listen("tcp", fmt.Sprintf(":%d", port))
+		if err != nil {
+			cancel()
+			return
+		}
+		t.Log("listener", listener.Addr())
+		defer listener.Close()
+		conn, err := listener.Accept()
+		if err != nil {
+			cancel()
+			return
+		}
+		defer conn.Close()
+	}()
+
+	dialer := RacingDialer(DialNoTimeout(), RetryDialUntilSuccess(10*time.Millisecond))
+	conn, err := dialer(ctx, "tcp", fmt.Sprintf("localhost:%d", port))
+	if err != nil {
+		t.Fatalf("failed to dial: %v", err)
+	}
+	conn.Close()
+	wg.Wait()
+}
diff --git a/pkg/api/rpc.go b/pkg/api/rpc.go
index 07d911c9..543e7eeb 100644
--- a/pkg/api/rpc.go
+++ b/pkg/api/rpc.go
@@ -6,6 +6,7 @@ import (
 	"net/http"
 	"os"
 	"strings"
+	"time"
 
 	"buf.build/gen/go/depot/api/connectrpc/go/depot/core/v1/corev1connect"
 	"connectrpc.com/connect"
@@ -84,8 +85,23 @@ func getHTTPClient(baseURL string) *http.Client {
 			},
 		}
 	}
-	// Use default client for HTTPS connections
-	return http.DefaultClient
+
+	t, ok := http.DefaultTransport.(*http.Transport)
+	if !ok {
+		return http.DefaultClient
+	}
+
+	transport := t.Clone()
+	transport.DialContext = RacingDialer(
+		RetryDialUntilSuccess(500*time.Millisecond),
+		DefaultHTTPDialer(),
+	)
+
+	racingClient := &http.Client{
+		Transport: transport,
+	}
+
+	return racingClient
 }
 
 func getBaseURL() string {