diff --git a/internal/pool/dial_conn_retry_test.go b/internal/pool/dial_conn_retry_test.go
new file mode 100644
index 000000000..61eba5b05
--- /dev/null
+++ b/internal/pool/dial_conn_retry_test.go
@@ -0,0 +1,208 @@
+package pool
+
+import (
+	"context"
+	"errors"
+	"net"
+	"sync/atomic"
+	"testing"
+	"time"
+)
+
+func TestDialConn_HangingDial_RetriesWithPerAttemptTimeout(t *testing.T) {
+	var calls atomic.Int32
+	var sawDeadline atomic.Int32
+
+	const (
+		dialTimeout = 50 * time.Millisecond
+		backoff     = 10 * time.Millisecond
+		retries     = 3
+	)
+
+	p := NewConnPool(&Options{
+		Dialer: func(ctx context.Context) (net.Conn, error) {
+			calls.Add(1)
+
+			// Ensure each attempt has a deadline (pool applies DialTimeout per attempt).
+			if dl, ok := ctx.Deadline(); ok {
+				rem := time.Until(dl)
+				// Very generous bounds to avoid flakes.
+				if rem > 5*time.Millisecond && rem <= 2*dialTimeout {
+					sawDeadline.Add(1)
+				}
+			}
+
+			// Simulate a TCP connect hang: block until the context cancels.
+			<-ctx.Done()
+			return nil, ctx.Err()
+		},
+		PoolSize:           1,
+		MaxConcurrentDials: 1,
+		DialTimeout:        dialTimeout,
+		DialerRetries:      retries,
+		DialerRetryTimeout: backoff,
+	})
+	defer p.Close()
+
+	// Use a parent context with a bounded timeout so this test fails fast (instead of hanging)
+	// when dialConn does not apply per-attempt DialTimeout via context.
+	parentBudget := dialTimeout*time.Duration(retries) + backoff*time.Duration(retries-1) + 250*time.Millisecond
+	ctx, cancel := context.WithTimeout(context.Background(), parentBudget)
+	defer cancel()
+
+	start := time.Now()
+	_, err := p.dialConn(ctx, true)
+	elapsed := time.Since(start)
+
+	if err == nil {
+		t.Fatalf("expected error")
+	}
+	if got := calls.Load(); got != retries {
+		t.Fatalf("expected %d dial attempts, got %d", retries, got)
+	}
+	if got := sawDeadline.Load(); got != retries {
+		t.Fatalf("expected deadline on all attempts, got %d/%d", got, retries)
+	}
+
+	// Each attempt should wait ~dialTimeout, plus backoff between attempts.
+	// Allow wide bounds for CI noise.
+	min := dialTimeout*time.Duration(retries) + backoff*time.Duration(retries-1)
+	if elapsed < min/2 {
+		t.Fatalf("dialConn returned too quickly (%v < %v), retries/backoff may not have occurred", elapsed, min/2)
+	}
+	if elapsed > 5*min {
+		t.Fatalf("dialConn took too long (%v > %v), likely hung beyond expected timeouts", elapsed, 5*min)
+	}
+}
+
+func TestDialConn_DoesNotExtendEarlierParentDeadline(t *testing.T) {
+	var calls atomic.Int32
+
+	p := NewConnPool(&Options{
+		Dialer: func(ctx context.Context) (net.Conn, error) {
+			calls.Add(1)
+			dl, ok := ctx.Deadline()
+			if !ok {
+				return nil, errors.New("expected deadline")
+			}
+			// Parent deadline should win (be soon).
+			if time.Until(dl) > 100*time.Millisecond {
+				return nil, errors.New("deadline was unexpectedly extended")
+			}
+			<-ctx.Done()
+			return nil, ctx.Err()
+		},
+		PoolSize:           1,
+		MaxConcurrentDials: 1,
+		DialTimeout:        500 * time.Millisecond,
+		DialerRetries:      1,
+	})
+	defer p.Close()
+
+	parent, cancel := context.WithTimeout(context.Background(), 30*time.Millisecond)
+	defer cancel()
+
+	_, err := p.dialConn(parent, true)
+	if err == nil {
+		t.Fatalf("expected error")
+	}
+	if got := calls.Load(); got != 1 {
+		t.Fatalf("expected 1 dial attempt, got %d", got)
+	}
+}
+
+func TestDialConn_ContextCancelStopsFurtherRetries(t *testing.T) {
+	var calls atomic.Int32
+
+	p := NewConnPool(&Options{
+		Dialer: func(ctx context.Context) (net.Conn, error) {
+			n := calls.Add(1)
+			if n == 1 {
+				// First attempt fails immediately; test cancels context to stop retries.
+				return nil, errors.New("dial failed")
+			}
+			return nil, errors.New("unexpected extra attempt")
+		},
+		PoolSize:           1,
+		MaxConcurrentDials: 1,
+		DialTimeout:        5 * time.Second,
+		DialerRetries:      5,
+		DialerRetryTimeout: 5 * time.Second,
+	})
+	defer p.Close()
+
+	ctx, cancel := context.WithCancel(context.Background())
+	// Cancel immediately after the first attempt fails by wrapping dialConn call.
+	// We do it via a goroutine so dialConn has a chance to enter the backoff select.
+	go func() {
+		// Give dialConn a moment to start. This avoids a race where ctx is already canceled
+		// before the first attempt and we wouldn't be testing the retry stop path.
+		time.Sleep(5 * time.Millisecond)
+		cancel()
+	}()
+
+	_, _ = p.dialConn(ctx, true)
+
+	if got := calls.Load(); got != 1 {
+		t.Fatalf("expected dialer to be called once after cancel, got %d", got)
+	}
+}
+
+func TestDialConn_DialTimeoutDisabled_DoesNotSetDeadline(t *testing.T) {
+	var calls atomic.Int32
+
+	p := NewConnPool(&Options{
+		Dialer: func(ctx context.Context) (net.Conn, error) {
+			calls.Add(1)
+			if _, ok := ctx.Deadline(); ok {
+				return nil, errors.New("unexpected deadline when DialTimeout disabled")
+			}
+			return nil, errors.New("dial failed")
+		},
+		PoolSize:           1,
+		MaxConcurrentDials: 1,
+		DialTimeout:        0,
+		DialerRetries:      1,
+	})
+	defer p.Close()
+
+	_, err := p.dialConn(context.Background(), true)
+	if err == nil {
+		t.Fatalf("expected error")
+	}
+	if got := calls.Load(); got != 1 {
+		t.Fatalf("expected 1 dial attempt, got %d", got)
+	}
+}
+
+func TestDialConn_NoBackoffAfterLastAttempt(t *testing.T) {
+	var calls atomic.Int32
+	backoff := 300 * time.Millisecond
+
+	p := NewConnPool(&Options{
+		Dialer: func(ctx context.Context) (net.Conn, error) {
+			calls.Add(1)
+			return nil, errors.New("dial failed")
+		},
+		PoolSize:           1,
+		MaxConcurrentDials: 1,
+		DialTimeout:        5 * time.Second,
+		DialerRetries:      1,
+		DialerRetryTimeout: backoff,
+	})
+	defer p.Close()
+
+	start := time.Now()
+	_, err := p.dialConn(context.Background(), true)
+	elapsed := time.Since(start)
+	if err == nil {
+		t.Fatalf("expected error")
+	}
+	if got := calls.Load(); got != 1 {
+		t.Fatalf("expected 1 dial attempt, got %d", got)
+	}
+	// If we slept after the last attempt, this will be ~backoff.
+	if elapsed >= backoff/2 {
+		t.Fatalf("dialConn took too long (%v); likely slept after last attempt (backoff=%v)", elapsed, backoff)
+	}
+}
diff --git a/internal/pool/dial_context_timeout_test.go b/internal/pool/dial_context_timeout_test.go
new file mode 100644
index 000000000..3c5e736ae
--- /dev/null
+++ b/internal/pool/dial_context_timeout_test.go
@@ -0,0 +1,40 @@
+package pool
+
+import (
+	"context"
+	"errors"
+	"net"
+	"testing"
+	"time"
+)
+
+// Ensures ConnPool applies DialTimeout per attempt via context (so dialing doesn't hang
+// when a custom dialer ignores timeouts).
+func TestDialConn_AppliesDialTimeoutPerAttemptViaContext(t *testing.T) {
+	p := NewConnPool(&Options{
+		Dialer: func(ctx context.Context) (net.Conn, error) {
+			// Pool should apply DialTimeout per attempt via context.
+			dl, ok := ctx.Deadline()
+			if !ok {
+				return nil, errors.New("expected context deadline")
+			}
+			remaining := time.Until(dl)
+			// Allow slack for scheduling jitter.
+			if remaining <= 50*time.Millisecond || remaining > 250*time.Millisecond {
+				return nil, errors.New("unexpected context deadline duration")
+			}
+			return nil, errors.New("dial failed")
+		},
+		PoolSize:           1,
+		MaxConcurrentDials: 1,
+		DialTimeout:        200 * time.Millisecond,
+		PoolTimeout:        10 * time.Millisecond,
+		DialerRetries:      1,
+	})
+	defer p.Close()
+
+	_, err := p.newConn(context.Background(), true)
+	if err == nil {
+		t.Fatalf("expected error")
+	}
+}
diff --git a/internal/pool/pool.go b/internal/pool/pool.go
index aaca530cb..d7d317954 100644
--- a/internal/pool/pool.go
+++ b/internal/pool/pool.go
@@ -456,10 +456,8 @@ func (p *ConnPool) checkMinIdleConns() {
 }
 
 func (p *ConnPool) addIdleConn() error {
-	ctx, cancel := context.WithTimeout(context.Background(), p.cfg.DialTimeout)
-	defer cancel()
-
-	cn, err := p.dialConn(ctx, true)
+	// Do not apply DialTimeout via context here; dialConn applies DialTimeout per attempt.
+	cn, err := p.dialConn(context.Background(), true)
 	if err != nil {
 		return err
 	}
@@ -505,9 +503,9 @@ func (p *ConnPool) newConn(ctx context.Context, pooled bool) (*Conn, error) {
 		ctx = context.Background()
 	}
 
-	dialCtx, cancel := context.WithTimeout(ctx, p.cfg.DialTimeout)
-	defer cancel()
-	cn, err := p.dialConn(dialCtx, pooled)
+	// Do not apply DialTimeout via context here; dialConn applies DialTimeout per attempt.
+	// We still propagate ctx so callers can cancel explicitly.
+	cn, err := p.dialConn(ctx, pooled)
 	if err != nil {
 		return nil, err
 	}
@@ -569,8 +567,8 @@ func (p *ConnPool) dialConn(ctx context.Context, pooled bool) (*Conn, error) {
 	}
 
 	// Retry dialing with backoff
-	// the context timeout is already handled by the context passed in
-	// so we may never reach the max retries, higher values don't hurt
+	// Dial timeout is applied per attempt (so retries/backoff don't eat into the next
+	// attempt's dial budget), while still honoring caller cancellation via ctx.
 	maxRetries := p.cfg.DialerRetries
 	if maxRetries <= 0 {
 		maxRetries = 5 // Default value
@@ -587,16 +585,31 @@ func (p *ConnPool) dialConn(ctx context.Context, pooled bool) (*Conn, error) {
 	// instead of a generic context deadline exceeded error
 	attempt := 0
 	for attempt = 0; (attempt < maxRetries) && shouldLoop; attempt++ {
-		netConn, err := p.cfg.Dialer(ctx)
+		attemptCtx := ctx
+		var cancel context.CancelFunc
+		if p.cfg.DialTimeout > 0 {
+			// Apply DialTimeout per attempt, but never extend an existing earlier deadline.
+			if deadline, ok := ctx.Deadline(); !ok || time.Until(deadline) > p.cfg.DialTimeout {
+				attemptCtx, cancel = context.WithTimeout(ctx, p.cfg.DialTimeout)
+			}
+		}
+
+		netConn, err := p.cfg.Dialer(attemptCtx)
+		if cancel != nil {
+			cancel()
+		}
 		if err != nil {
 			lastErr = err
 			// Add backoff delay for retry attempts
 			// (not for the first attempt, do at least one)
-			select {
-			case <-ctx.Done():
-				shouldLoop = false
-			case <-time.After(backoffDuration):
-				// Continue with retry
+			// Do not sleep after the last attempt.
+			if attempt+1 < maxRetries {
+				select {
+				case <-ctx.Done():
+					shouldLoop = false
+				case <-time.After(backoffDuration):
+					// Continue with retry
+				}
 			}
 			continue
 		}
@@ -648,19 +661,26 @@ func (p *ConnPool) tryDial() {
 			return
 		}
 
-		ctx, cancel := context.WithTimeout(context.Background(), p.cfg.DialTimeout)
+		// Probe dialing even when dialErrorsNum is saturated. Apply DialTimeout per probe
+		// attempt so custom dialers can't hang indefinitely.
+		ctx := context.Background()
+		var cancel context.CancelFunc
+		if p.cfg.DialTimeout > 0 {
+			ctx, cancel = context.WithTimeout(ctx, p.cfg.DialTimeout)
+		}
 
 		conn, err := p.cfg.Dialer(ctx)
+		if cancel != nil {
+			cancel()
+		}
 		if err != nil {
 			p.setLastDialError(err)
 			time.Sleep(time.Second)
-			cancel()
 			continue
 		}
 
 		atomic.StoreUint32(&p.dialErrorsNum, 0)
 		_ = conn.Close()
-		cancel()
 		return
 	}
 }
@@ -835,7 +855,8 @@ func (p *ConnPool) queuedNewConn(ctx context.Context) (*Conn, error) {
 		return nil, ctx.Err()
 	}
 
-	dialCtx, cancel := context.WithTimeout(context.Background(), p.cfg.DialTimeout)
+	// Don't apply DialTimeout via context here; dialConn applies DialTimeout per attempt.
+	dialCtx, cancel := context.WithCancel(context.Background())
 
 	w := &wantConn{
 		ctx:       dialCtx,
diff --git a/internal/pool/try_dial_test.go b/internal/pool/try_dial_test.go
new file mode 100644
index 000000000..b20b62f1e
--- /dev/null
+++ b/internal/pool/try_dial_test.go
@@ -0,0 +1,81 @@
+package pool
+
+import (
+	"context"
+	"errors"
+	"net"
+	"testing"
+	"time"
+)
+
+func TestTryDial_AppliesDialTimeoutWhenSet(t *testing.T) {
+	p := NewConnPool(&Options{
+		Dialer: func(ctx context.Context) (net.Conn, error) {
+			if _, ok := ctx.Deadline(); !ok {
+				return nil, errors.New("expected deadline in tryDial")
+			}
+			c1, c2 := net.Pipe()
+			_ = c2.Close()
+			return c1, nil
+		},
+		PoolSize:           1,
+		MaxConcurrentDials: 1,
+		DialTimeout:        200 * time.Millisecond,
+	})
+	defer p.Close()
+
+	p.tryDial()
+}
+
+func TestTryDial_DoesNotApplyDialTimeoutWhenDisabled(t *testing.T) {
+	p := NewConnPool(&Options{
+		Dialer: func(ctx context.Context) (net.Conn, error) {
+			if _, ok := ctx.Deadline(); ok {
+				return nil, errors.New("unexpected deadline in tryDial when DialTimeout disabled")
+			}
+			// Ensure context is still a real context.
+			select {
+			case <-ctx.Done():
+				return nil, ctx.Err()
+			default:
+			}
+
+			c1, c2 := net.Pipe()
+			_ = c2.Close()
+			return c1, nil
+		},
+		PoolSize:           1,
+		MaxConcurrentDials: 1,
+		DialTimeout:        0,
+	})
+	defer p.Close()
+
+	p.tryDial()
+}
+
+func TestTryDial_RespectsPoolClose(t *testing.T) {
+	// If Dialer keeps failing, tryDial should exit once the pool is closed.
+	p := NewConnPool(&Options{
+		Dialer: func(ctx context.Context) (net.Conn, error) {
+			return nil, errors.New("dial failed")
+		},
+		PoolSize:           1,
+		MaxConcurrentDials: 1,
+		DialTimeout:        10 * time.Millisecond,
+	})
+
+	done := make(chan struct{})
+	go func() {
+		p.tryDial()
+		close(done)
+	}()
+
+	time.Sleep(20 * time.Millisecond)
+	_ = p.Close()
+
+	select {
+	case <-done:
+	case <-time.After(2 * time.Second):
+		t.Fatalf("tryDial did not exit after pool close")
+	}
+}