diff --git a/go.mod b/go.mod
index 723c257..34eeedc 100644
--- a/go.mod
+++ b/go.mod
@@ -7,6 +7,7 @@ require (
 	charm.land/bubbletea/v2 v2.0.6
 	github.com/BurntSushi/toml v1.6.0
 	github.com/aymanbagabas/go-udiff v0.4.1
+	github.com/cenkalti/backoff/v4 v4.3.0
 	github.com/coder/websocket v1.8.14
 	github.com/dustinkirkland/golang-petname v0.0.0-20260215035315-f0c533e9ce9b
 	github.com/gin-gonic/gin v1.12.0
diff --git a/go.sum b/go.sum
index 230f936..cd054a9 100644
--- a/go.sum
+++ b/go.sum
@@ -140,6 +140,8 @@ github.com/catenacyber/perfsprint v0.10.1 h1:u7Riei30bk46XsG8nknMhKLXG9BcXz3+3tl
 github.com/catenacyber/perfsprint v0.10.1/go.mod h1:DJTGsi/Zufpuus6XPGJyKOTMELe347o6akPvWG9Zcsc=
 github.com/ccojocar/zxcvbn-go v1.0.4 h1:FWnCIRMXPj43ukfX000kvBZvV6raSxakYr1nzyNrUcc=
 github.com/ccojocar/zxcvbn-go v1.0.4/go.mod h1:3GxGX+rHmueTUMvm5ium7irpyjmm7ikxYFOSJB21Das=
+github.com/cenkalti/backoff/v4 v4.3.0 h1:MyRJ/UdXutAwSAT+s3wNd7MfTIcy71VQueUuFK343L8=
+github.com/cenkalti/backoff/v4 v4.3.0/go.mod h1:Y3VNntkOUPxTVeUxJ/G5vcM//AlwfmyYozVcomhLiZE=
 github.com/census-instrumentation/opencensus-proto v0.2.1/go.mod h1:f6KPmirojxKA12rnyqOA5BBL4O983OfeGPqjHWSTneU=
 github.com/cespare/xxhash/v2 v2.1.1/go.mod h1:VGX0DQ3Q6kWi7AoAeZDth3/j3BFtOZR5XLFGgcrjCOs=
 github.com/cespare/xxhash/v2 v2.1.2/go.mod h1:VGX0DQ3Q6kWi7AoAeZDth3/j3BFtOZR5XLFGgcrjCOs=
diff --git a/internal/sidecar/ssh.go b/internal/sidecar/ssh.go
index 02afe87..36f490b 100644
--- a/internal/sidecar/ssh.go
+++ b/internal/sidecar/ssh.go
@@ -16,12 +16,16 @@ import (
 	"path/filepath"
 	"sort"
 	"strings"
+	"syscall"
+	"time"
 
+	"github.com/cenkalti/backoff/v4"
 	"github.com/coder/websocket"
 	"golang.org/x/crypto/ssh"
 	"golang.org/x/term"
 
 	"github.com/CircleCI-Public/chunk-cli/internal/closer"
+	"github.com/CircleCI-Public/chunk-cli/internal/iostream"
 )
 
 // ExecResult holds the output of a command executed over SSH.
@@ -336,3 +340,62 @@ func tofuHostKeyCallback(knownHostsPath, host string) ssh.HostKeyCallback {
 		return err
 	}
 }
+
+// waitForSSHReady probes the SSH connection with exponential backoff, retrying
+// on transient errors so a newly-created sidecar has time to finish booting
+// before its SSH service accepts connections.
+func waitForSSHReady(ctx context.Context, session *Session, status iostream.StatusFunc) error {
+	return waitForSSHReadyWithDial(ctx, session, status, dialSSH)
+}
+
+// waitForSSHReadyWithDial is the underlying implementation; dialFn is injectable
+// for testing the retry control flow without a live network.
+func waitForSSHReadyWithDial(
+	ctx context.Context,
+	session *Session,
+	status iostream.StatusFunc,
+	dialFn func(context.Context, *Session) (*sshConn, error),
+) error {
+	b := backoff.NewExponentialBackOff()
+	b.InitialInterval = 2 * time.Second
+	b.MaxInterval = 15 * time.Second
+	b.MaxElapsedTime = 90 * time.Second
+
+	notified := false
+	return backoff.RetryNotify(
+		func() error {
+			conn, err := dialFn(ctx, session)
+			if err != nil {
+				if !isTransientSSHError(err) {
+					return backoff.Permanent(err)
+				}
+				return err
+			}
+			if conn != nil {
+				_ = conn.Close()
+			}
+			return nil
+		},
+		backoff.WithContext(b, ctx),
+		func(_ error, _ time.Duration) {
+			if !notified {
+				status(iostream.LevelInfo, "Waiting for sidecar SSH to become available...")
+				notified = true
+			}
+		},
+	)
+}
+
+// isTransientSSHError reports whether err is a network-level error worth
+// retrying when dialling the sidecar SSH service — specifically connection
+// refused and timeouts that indicate the daemon is not yet ready.
+func isTransientSSHError(err error) bool {
+	var netErr net.Error
+	if !errors.As(err, &netErr) {
+		return false
+	}
+	if netErr.Timeout() {
+		return true
+	}
+	return errors.Is(err, syscall.ECONNREFUSED)
+}
diff --git a/internal/sidecar/sync.go b/internal/sidecar/sync.go
index 5d491c9..6891eee 100644
--- a/internal/sidecar/sync.go
+++ b/internal/sidecar/sync.go
@@ -56,6 +56,9 @@ func Sync(ctx context.Context,
 	if err != nil {
 		return err
 	}
+	if err := waitForSSHReady(ctx, session, status); err != nil {
+		return err
+	}
 
 	cwd, err := os.Getwd()
 	if err != nil {
diff --git a/internal/sidecar/sync_whitebox_test.go b/internal/sidecar/sync_whitebox_test.go
new file mode 100644
index 0000000..901c87e
--- /dev/null
+++ b/internal/sidecar/sync_whitebox_test.go
@@ -0,0 +1,174 @@
+package sidecar
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"net"
+	"os"
+	"path/filepath"
+	"syscall"
+	"testing"
+
+	"gotest.tools/v3/assert"
+
+	"github.com/CircleCI-Public/chunk-cli/internal/circleci"
+	"github.com/CircleCI-Public/chunk-cli/internal/iostream"
+	"github.com/CircleCI-Public/chunk-cli/internal/testing/fakes"
+)
+
+func TestIsTransientSSHError(t *testing.T) {
+	t.Run("timeout is transient", func(t *testing.T) {
+		err := &net.OpError{Op: "dial", Err: &timeoutError{}}
+		assert.Equal(t, isTransientSSHError(err), true)
+	})
+
+	t.Run("connection refused is transient", func(t *testing.T) {
+		err := &net.OpError{
+			Op:  "dial",
+			Net: "tcp",
+			Err: &os.SyscallError{Syscall: "connect", Err: syscall.ECONNREFUSED},
+		}
+		assert.Equal(t, isTransientSSHError(err), true)
+	})
+
+	t.Run("connection refused wrapped with fmt.Errorf is transient", func(t *testing.T) {
+		inner := &net.OpError{
+			Op:  "dial",
+			Net: "tcp",
+			Err: &os.SyscallError{Syscall: "connect", Err: syscall.ECONNREFUSED},
+		}
+		err := fmt.Errorf("websocket connect: %w", inner)
+		assert.Equal(t, isTransientSSHError(err), true)
+	})
+
+	t.Run("timeout wrapped with fmt.Errorf is transient", func(t *testing.T) {
+		inner := &net.OpError{Op: "dial", Err: &timeoutError{}}
+		err := fmt.Errorf("register SSH key: %w", inner)
+		assert.Equal(t, isTransientSSHError(err), true)
+	})
+
+	t.Run("unreachable host is not transient", func(t *testing.T) {
+		err := &net.OpError{
+			Op:  "dial",
+			Net: "tcp",
+			Err: &os.SyscallError{Syscall: "connect", Err: syscall.EHOSTUNREACH},
+		}
+		assert.Equal(t, isTransientSSHError(err), false)
+	})
+
+	t.Run("ErrNotAuthorized is not transient", func(t *testing.T) {
+		err := fmt.Errorf("add ssh key: %w", circleci.ErrNotAuthorized)
+		assert.Equal(t, isTransientSSHError(err), false)
+	})
+
+	t.Run("StatusError is not transient", func(t *testing.T) {
+		err := &circleci.StatusError{Op: "add ssh key", StatusCode: 503}
+		assert.Equal(t, isTransientSSHError(err), false)
+	})
+
+	t.Run("KeyNotFoundError is not transient", func(t *testing.T) {
+		err := &KeyNotFoundError{Path: "/home/user/.ssh/chunk_ai"}
+		assert.Equal(t, isTransientSSHError(err), false)
+	})
+
+	t.Run("PublicKeyNotFoundError is not transient", func(t *testing.T) {
+		err := &PublicKeyNotFoundError{KeyPath: "/home/user/.ssh/chunk_ai.pub"}
+		assert.Equal(t, isTransientSSHError(err), false)
+	})
+
+	t.Run("generic error is not transient", func(t *testing.T) {
+		err := fmt.Errorf("resolve home directory: permission denied")
+		assert.Equal(t, isTransientSSHError(err), false)
+	})
+}
+
+func TestWaitForSSHReady(t *testing.T) {
+	t.Run("succeeds immediately when SSH server is ready", func(t *testing.T) {
+		keyFile, pubKey := fakes.GenerateSSHKeypair(t)
+		sshSrv := fakes.NewSSHServer(t, pubKey)
+
+		session := &Session{
+			URL:          sshSrv.Addr(),
+			IdentityFile: keyFile,
+			KnownHosts:   filepath.Join(t.TempDir(), "known_hosts"),
+		}
+
+		var notified bool
+		statusFn := iostream.StatusFunc(func(_ iostream.Level, _ string) { notified = true })
+
+		err := waitForSSHReady(context.Background(), session, statusFn)
+		assert.NilError(t, err)
+		assert.Equal(t, notified, false, "no retry should be needed when SSH is already ready")
+	})
+
+	t.Run("permanent error returns immediately without notifying", func(t *testing.T) {
+		permanentErr := errors.New("ssh handshake: auth failed")
+
+		var notifications int
+		statusFn := iostream.StatusFunc(func(_ iostream.Level, _ string) { notifications++ })
+
+		err := waitForSSHReadyWithDial(context.Background(), &Session{}, statusFn,
+			func(_ context.Context, _ *Session) (*sshConn, error) {
+				return nil, permanentErr // not a net.Error → permanent
+			},
+		)
+		assert.ErrorIs(t, err, permanentErr)
+		assert.Equal(t, notifications, 0, "permanent error should not trigger retry notification")
+	})
+
+	t.Run("retries on transient error and notifies exactly once", func(t *testing.T) {
+		transientErr := &net.OpError{
+			Op:  "dial",
+			Net: "tcp",
+			Err: &os.SyscallError{Syscall: "connect", Err: syscall.ECONNREFUSED},
+		}
+
+		ctx, cancel := context.WithCancel(context.Background())
+		defer cancel()
+
+		var notifications int
+		statusFn := iostream.StatusFunc(func(_ iostream.Level, _ string) {
+			notifications++
+			cancel() // stop retrying after the first notification
+		})
+
+		err := waitForSSHReadyWithDial(ctx, &Session{}, statusFn,
+			func(_ context.Context, _ *Session) (*sshConn, error) {
+				return nil, transientErr
+			},
+		)
+		assert.Assert(t, err != nil, "should return an error when retries are stopped")
+		assert.Equal(t, notifications, 1, "status should be notified exactly once regardless of retry count")
+	})
+
+	t.Run("succeeds after transient errors resolve", func(t *testing.T) {
+		transientErr := &net.OpError{
+			Op:  "dial",
+			Net: "tcp",
+			Err: &os.SyscallError{Syscall: "connect", Err: syscall.ECONNREFUSED},
+		}
+
+		attempts := 0
+		statusFn := iostream.StatusFunc(func(_ iostream.Level, _ string) {})
+
+		err := waitForSSHReadyWithDial(context.Background(), &Session{}, statusFn,
+			func(_ context.Context, _ *Session) (*sshConn, error) {
+				attempts++
+				if attempts < 3 {
+					return nil, transientErr
+				}
+				return nil, nil // success: SSH is now ready
+			},
+		)
+		assert.NilError(t, err)
+		assert.Equal(t, attempts, 3, "should have retried until success")
+	})
+}
+
+// timeoutError is a net.Error that reports Timeout() == true.
+type timeoutError struct{}
+
+func (timeoutError) Error() string   { return "i/o timeout" }
+func (timeoutError) Timeout() bool   { return true }
+func (timeoutError) Temporary() bool { return true }