diff --git a/README.md b/README.md
index 4fee48c43..e6dec8f8e 100644
--- a/README.md
+++ b/README.md
@@ -159,6 +159,21 @@ Local settings override project settings field-by-field. When you run `entire st
 | "shadow branch conflict" | Run `entire rewind reset --force` |
 | "session not found" | Check available sessions with `entire session list` |
 
+### SSH Authentication Errors
+
+If you see an error like this when running `entire resume`:
+
+```
+Failed to fetch metadata: failed to fetch entire/sessions from origin: ssh: handshake failed: ssh: unable to authenticate, attempted methods [none publickey], no supported methods remain
+```
+
+This is a [known issue with go-git's SSH handling](https://github.com/go-git/go-git/issues/411). Fix it by adding GitHub's host keys to your known_hosts file:
+
+```bash
+ssh-keyscan -t rsa github.com > ~/.ssh/known_hosts
+ssh-keyscan -t ecdsa github.com >> ~/.ssh/known_hosts
+```
+
 ### Debug Mode
 
 ```bash
diff --git a/cmd/entire/cli/git_operations.go b/cmd/entire/cli/git_operations.go
index 3b0e3e8de..033a09948 100644
--- a/cmd/entire/cli/git_operations.go
+++ b/cmd/entire/cli/git_operations.go
@@ -7,6 +7,7 @@ import (
 	"os/exec"
 	"strings"
 
+	"entire.io/cli/cmd/entire/cli/paths"
 	"entire.io/cli/cmd/entire/cli/strategy"
 
 	"github.com/go-git/go-git/v5"
@@ -365,3 +366,42 @@ func FetchAndCheckoutRemoteBranch(branchName string) error {
 	// Checkout the new local branch
 	return CheckoutBranch(branchName)
 }
+
+// FetchMetadataBranch fetches the entire/sessions branch from origin and creates/updates the local branch.
+// This is used when the metadata branch exists on remote but not locally.
+func FetchMetadataBranch() error {
+	repo, err := openRepository()
+	if err != nil {
+		return fmt.Errorf("failed to open repository: %w", err)
+	}
+
+	branchName := paths.MetadataBranchName
+
+	// Fetch the specific branch from origin
+	remote, err := repo.Remote("origin")
+	if err != nil {
+		return fmt.Errorf("failed to get origin remote: %w", err)
+	}
+
+	refSpec := fmt.Sprintf("+refs/heads/%s:refs/remotes/origin/%s", branchName, branchName)
+	err = remote.Fetch(&git.FetchOptions{
+		RefSpecs: []config.RefSpec{config.RefSpec(refSpec)},
+	})
+	if err != nil && !errors.Is(err, git.NoErrAlreadyUpToDate) {
+		return fmt.Errorf("failed to fetch %s from origin: %w", branchName, err)
+	}
+
+	// Get the remote branch reference
+	remoteRef, err := repo.Reference(plumbing.NewRemoteReferenceName("origin", branchName), true)
+	if err != nil {
+		return fmt.Errorf("branch '%s' not found on origin: %w", branchName, err)
+	}
+
+	// Create or update local branch pointing to the same commit
+	localRef := plumbing.NewHashReference(plumbing.NewBranchReferenceName(branchName), remoteRef.Hash())
+	if err := repo.Storer.SetReference(localRef); err != nil {
+		return fmt.Errorf("failed to create local %s branch: %w", branchName, err)
+	}
+
+	return nil
+}
diff --git a/cmd/entire/cli/resume.go b/cmd/entire/cli/resume.go
index f1e354b13..13dedc17c 100644
--- a/cmd/entire/cli/resume.go
+++ b/cmd/entire/cli/resume.go
@@ -87,7 +87,8 @@ func runResume(branchName string, force bool) error {
 		// Fetch and checkout the remote branch
 		fmt.Fprintf(os.Stderr, "Fetching branch '%s' from origin...\n", branchName)
 		if err := FetchAndCheckoutRemoteBranch(branchName); err != nil {
-			return err
+			fmt.Fprintf(os.Stderr, "Failed to checkout branch: %v\n", err)
+			return NewSilentError(errors.New("failed to checkout branch"))
 		}
 		fmt.Fprintf(os.Stderr, "Switched to branch '%s'\n", branchName)
 	} else {
@@ -102,7 +103,8 @@ func runResume(branchName string, force bool) error {
 
 		// Checkout the branch
 		if err := CheckoutBranch(branchName); err != nil {
-			return err
+			fmt.Fprintf(os.Stderr, "Failed to checkout branch: %v\n", err)
+			return NewSilentError(errors.New("failed to checkout branch"))
 		}
 		fmt.Fprintf(os.Stderr, "Switched to branch '%s'\n", branchName)
 	}
@@ -314,7 +316,7 @@ func promptResumeFromOlderCheckpoint() (bool, error) {
 }
 
 // checkRemoteMetadata checks if checkpoint metadata exists on origin/entire/sessions
-// and provides guidance to the user.
+// and automatically fetches it if available.
 func checkRemoteMetadata(repo *git.Repository, checkpointID string) error {
 	// Try to get remote metadata branch tree
 	remoteTree, err := strategy.GetRemoteMetadataBranchTree(repo)
@@ -325,18 +327,22 @@ func checkRemoteMetadata(repo *git.Repository, checkpointID string) error {
 	}
 
 	// Check if the checkpoint exists on the remote
-	_, err = strategy.ReadCheckpointMetadata(remoteTree, paths.CheckpointPath(checkpointID))
+	metadata, err := strategy.ReadCheckpointMetadata(remoteTree, paths.CheckpointPath(checkpointID))
 	if err != nil {
 		fmt.Fprintf(os.Stderr, "Checkpoint '%s' found in commit but session metadata not available\n", checkpointID)
 		return nil //nolint:nilerr // Informational message, not a fatal error
 	}
 
-	// Metadata exists on remote but not locally
-	fmt.Fprintf(os.Stderr, "Checkpoint '%s' found in commit but session metadata not available locally\n", checkpointID)
-	fmt.Fprintf(os.Stderr, "The metadata exists on origin. To fetch it, run:\n")
-	fmt.Fprintf(os.Stderr, "  git fetch origin entire/sessions:entire/sessions\n")
-	fmt.Fprintf(os.Stderr, "\nThen run this command again.\n")
-	return nil
+	// Metadata exists on remote but not locally - fetch it automatically
+	fmt.Fprintf(os.Stderr, "Fetching session metadata from origin...\n")
+	if err := FetchMetadataBranch(); err != nil {
+		fmt.Fprintf(os.Stderr, "Failed to fetch metadata: %v\n", err)
+		fmt.Fprintf(os.Stderr, "You can try manually: git fetch origin entire/sessions:entire/sessions\n")
+		return NewSilentError(errors.New("failed to fetch metadata"))
+	}
+
+	// Now resume the session with the fetched metadata
+	return resumeSession(metadata.SessionID, checkpointID, false)
 }
 
 // resumeSession restores and displays the resume command for a specific session.
diff --git a/cmd/entire/cli/resume_test.go b/cmd/entire/cli/resume_test.go
index 7b097cdb0..926fb636d 100644
--- a/cmd/entire/cli/resume_test.go
+++ b/cmd/entire/cli/resume_test.go
@@ -1,6 +1,7 @@
 package cli
 
 import (
+	"errors"
 	"fmt"
 	"os"
 	"path/filepath"
@@ -496,12 +497,18 @@ func TestCheckRemoteMetadata_MetadataExistsOnRemote(t *testing.T) {
 		t.Fatalf("Failed to remove local metadata branch: %v", err)
 	}
 
-	// Call checkRemoteMetadata - should find it on remote and suggest fetch
+	// Call checkRemoteMetadata - should find it on remote and attempt to fetch
+	// In this test environment without a real origin remote, the fetch will fail
+	// but it should return a SilentError (user-friendly error message already printed)
 	err = checkRemoteMetadata(repo, checkpointID)
-	if err != nil {
-		t.Errorf("checkRemoteMetadata() returned error: %v", err)
+	if err == nil {
+		t.Error("checkRemoteMetadata() should return SilentError when fetch fails")
+	} else {
+		var silentErr *SilentError
+		if !errors.As(err, &silentErr) {
+			t.Errorf("checkRemoteMetadata() should return SilentError, got: %v", err)
+		}
 	}
-	// Note: We can't easily capture stderr in this test, but the function should not error
 }
 
 func TestCheckRemoteMetadata_NoRemoteMetadataBranch(t *testing.T) {
@@ -611,10 +618,16 @@ func TestResumeFromCurrentBranch_FallsBackToRemote(t *testing.T) {
 		t.Fatalf("Failed to create commit with checkpoint: %v", err)
 	}
 
-	// Run resumeFromCurrentBranch - should fall back to remote and suggest fetch
+	// Run resumeFromCurrentBranch - should fall back to remote and attempt fetch
+	// In this test environment without a real origin remote, the fetch will fail
+	// but it should return a SilentError (user-friendly error message already printed)
 	err = resumeFromCurrentBranch("master", false)
-	if err != nil {
-		t.Errorf("resumeFromCurrentBranch() returned error when falling back to remote: %v", err)
+	if err == nil {
+		t.Error("resumeFromCurrentBranch() should return SilentError when fetch fails")
+	} else {
+		var silentErr *SilentError
+		if !errors.As(err, &silentErr) {
+			t.Errorf("resumeFromCurrentBranch() should return SilentError, got: %v", err)
+		}
 	}
-	// The function should print the fetch suggestion to stderr (can't easily verify output)
 }