diff --git a/cmd/cmd.go b/cmd/cmd.go
index ce7187aee..91b278db9 100644
--- a/cmd/cmd.go
+++ b/cmd/cmd.go
@@ -8,6 +8,7 @@ import (
 	"crypto/ed25519"
 	"crypto/rand"
 	"crypto/sha256"
+	"encoding/base64"
 	"encoding/pem"
 	"errors"
 	"fmt"
@@ -16,6 +17,7 @@ import (
 	"math"
 	"net"
 	"net/http"
+	"net/url"
 	"os"
 	"os/signal"
 	"path/filepath"
@@ -30,6 +32,7 @@ import (
 	"github.com/containerd/console"
 	"github.com/mattn/go-runewidth"
 	"github.com/olekukonko/tablewriter"
+	"github.com/pkg/browser"
 	"github.com/spf13/cobra"
 	"golang.org/x/crypto/ssh"
 	"golang.org/x/term"
@@ -516,7 +519,26 @@ func RunHandler(cmd *cobra.Command, args []string) error {
 	return generate(cmd, opts)
 }
 
-func errFromUnknownKey(unknownKeyErr error) error {
+func generateFingerprint(key string) string {
+	hash := sha256.Sum256([]byte(key))
+	fingerprint := base64.RawURLEncoding.EncodeToString(hash[:6])
+
+	var formatted strings.Builder
+	for i, char := range fingerprint {
+		if i > 0 && i%2 == 0 {
+			formatted.WriteRune('-')
+		}
+		formatted.WriteRune(char)
+	}
+
+	return formatted.String()
+}
+
+// tryConnect handles key validation when a connection fails due to an unknown key.
+// It attempts to open the browser for interactive sessions to let users connect their key,
+// falling back to command-line instructions for non-interactive sessions.
+// Returns nil if browser flow succeeds, or an error with connection instructions otherwise.
+func tryConnect(unknownKeyErr error) error {
 	// find SSH public key in the error message
 	// TODO (brucemacd): the API should return structured errors so that this message parsing isn't needed
 	sshKeyPattern := `ssh-\w+ [^\s"]+`
@@ -545,14 +567,23 @@ func errFromUnknownKey(unknownKeyErr error) error {
 			return unknownKeyErr
 		}
 
-		var msg strings.Builder
-		msg.WriteString(unknownKeyErr.Error())
-		msg.WriteString("\n\nYour ollama key is:\n")
-		msg.WriteString(localPubKey)
-		msg.WriteString("\nAdd your key at:\n")
-		msg.WriteString("https://ollama.com/settings/keys")
+		if term.IsTerminal(int(os.Stdout.Fd())) {
+			// URL encode the key and device name for the browser URL
+			encodedKey := base64.RawURLEncoding.EncodeToString([]byte(localPubKey))
+			d, _ := os.Hostname()
+			encodedDevice := url.QueryEscape(d)
+			browserURL := fmt.Sprintf("https://ollama.com/connect?host=%s&key=%s", encodedDevice, encodedKey)
 
-		return errors.New(msg.String())
+			if err := browser.OpenURL(browserURL); err == nil {
+				fmt.Printf("\nOpening browser to add your key...\n")
+				fmt.Printf("\nCheck that this code matches what is shown in your browser:\n")
+				fmt.Printf("\n    %s\n", generateFingerprint(localPubKey))
+				return nil
+			}
+		}
+
+		// only return error for non-interactive terminals or if browser opening failed
+		return fmt.Errorf("%s\nAdd your key at:\nhttps://ollama.com/settings/keys", unknownKeyErr.Error())
 	}
 
 	return unknownKeyErr
@@ -611,13 +642,16 @@ func PushHandler(cmd *cobra.Command, args []string) error {
 		if spinner != nil {
 			spinner.Stop()
 		}
+		if p != nil {
+			p.Stop()
+		}
 		if strings.Contains(err.Error(), "access denied") {
 			return errors.New("you are not authorized to push to this namespace, create the model under a namespace you own")
 		}
 		if strings.Contains(err.Error(), errtypes.UnknownOllamaKeyErrMsg) && isOllamaHost {
 			// the user has not added their ollama key to ollama.com
 			// return an error with a more user-friendly message
-			return errFromUnknownKey(err)
+			return tryConnect(err)
 		}
 		return err
 	}
diff --git a/go.mod b/go.mod
index 496d8d3ab..f56a221bb 100644
--- a/go.mod
+++ b/go.mod
@@ -22,6 +22,7 @@ require (
 	github.com/mattn/go-runewidth v0.0.14
 	github.com/nlpodyssey/gopickle v0.3.0
 	github.com/pdevine/tensor v0.0.0-20240510204454-f88f4562727c
+	github.com/pkg/browser v0.0.0-20240102092130-5ac0b6a4141c
 	golang.org/x/image v0.22.0
 )
 
diff --git a/go.sum b/go.sum
index b3093ceb9..04332cf15 100644
--- a/go.sum
+++ b/go.sum
@@ -159,6 +159,8 @@ github.com/phpdave11/gofpdf v1.4.2/go.mod h1:zpO6xFn9yxo3YLyMvW8HcKWVdbNqgIfOOp2
 github.com/phpdave11/gofpdi v1.0.12/go.mod h1:vBmVV0Do6hSBHC8uKUQ71JGW+ZGQq74llk/7bXwjDoI=
 github.com/pierrec/lz4/v4 v4.1.8 h1:ieHkV+i2BRzngO4Wd/3HGowuZStgq6QkPsD1eolNAO4=
 github.com/pierrec/lz4/v4 v4.1.8/go.mod h1:gZWDp/Ze/IJXGXf23ltt2EXimqmTUXEy0GFuRQyBid4=
+github.com/pkg/browser v0.0.0-20240102092130-5ac0b6a4141c h1:+mdjkGKdHQG3305AYmdv1U2eRNDiU2ErMBj1gwrq8eQ=
+github.com/pkg/browser v0.0.0-20240102092130-5ac0b6a4141c/go.mod h1:7rwL4CYBLnjLxUqIJNnCWiEdr3bn6IUYi15bNlnbCCU=
 github.com/pkg/errors v0.8.1/go.mod h1:bwawxfHBFNV+L2hUp1rHADufV3IMtnDRdf1r5NINEl0=
 github.com/pkg/errors v0.9.1 h1:FEBLx1zS214owpjy7qsBeixbURkuhQAwrK5UwLGTwt4=
 github.com/pkg/errors v0.9.1/go.mod h1:bwawxfHBFNV+L2hUp1rHADufV3IMtnDRdf1r5NINEl0=