diff --git a/cmd/pro/login.go b/cmd/pro/login.go
index aec76a098..c271ee9ae 100644
--- a/cmd/pro/login.go
+++ b/cmd/pro/login.go
@@ -2,9 +2,7 @@ package pro
 
 import (
 	"context"
-	"encoding/json"
 	"fmt"
-	"io"
 	"net/url"
 	"path/filepath"
 	"strings"
@@ -12,7 +10,7 @@ import (
 	proflags "github.com/loft-sh/devpod/cmd/pro/flags"
 	providercmd "github.com/loft-sh/devpod/cmd/provider"
 	"github.com/loft-sh/devpod/pkg/config"
-	"github.com/loft-sh/devpod/pkg/http"
+	"github.com/loft-sh/devpod/pkg/loft"
 	"github.com/loft-sh/devpod/pkg/loft/client"
 	"github.com/loft-sh/devpod/pkg/provider"
 	"github.com/loft-sh/devpod/pkg/types"
@@ -222,33 +220,11 @@ func (cmd *LoginCmd) resolveProviderSource(url string) error {
 		return nil
 	}
 
-	resp, err := http.GetHTTPClient().Get(url + "/version")
+	version, err := loft.GetDevPodVersion(url)
 	if err != nil {
-		return fmt.Errorf("get %s: %w", url, err)
-	} else if resp.StatusCode != 200 {
-		out, _ := io.ReadAll(resp.Body)
-		return fmt.Errorf("get %s: %s (Status: %d)", url, string(out), resp.StatusCode)
+		return fmt.Errorf("get version: %w", err)
 	}
-
-	versionRaw, err := io.ReadAll(resp.Body)
-	if err != nil {
-		return fmt.Errorf("read %s: %w", url, err)
-	}
-
-	version := &versionObject{}
-	err = json.Unmarshal(versionRaw, version)
-	if err != nil {
-		return fmt.Errorf("parse %s: %w", url, err)
-	} else if version.DevPodVersion == "" {
-		return fmt.Errorf("unexpected version '%s', please use --version to define a provider version", version.DevPodVersion)
-	}
-
-	// make sure it starts with a v
-	if !strings.HasPrefix(version.DevPodVersion, "v") {
-		version.DevPodVersion = "v" + version.DevPodVersion
-	}
-
-	cmd.ProviderSource = providerRepo + "@" + version.DevPodVersion
+	cmd.ProviderSource = providerRepo + "@" + version
 
 	return nil
 }
@@ -299,11 +275,6 @@ func LoftConfigPath(devPodConfig *config.Config, providerName string) (string, e
 	return configPath, nil
 }
 
-type versionObject struct {
-	// Version is the remote devpod version
-	DevPodVersion string `json:"devPodVersion,omitempty"`
-}
-
 var fallbackProvider = `name: devpod-pro
 version: v0.0.0
 icon: https://devpod.sh/assets/devpod.svg
diff --git a/cmd/up.go b/cmd/up.go
index 0a9e8e414..7247bfbe2 100644
--- a/cmd/up.go
+++ b/cmd/up.go
@@ -12,6 +12,7 @@ import (
 	"strconv"
 	"strings"
 
+	"github.com/blang/semver"
 	"github.com/loft-sh/devpod/cmd/flags"
 	"github.com/loft-sh/devpod/pkg/agent"
 	"github.com/loft-sh/devpod/pkg/agent/tunnelserver"
@@ -26,6 +27,7 @@ import (
 	"github.com/loft-sh/devpod/pkg/ide/jupyter"
 	"github.com/loft-sh/devpod/pkg/ide/openvscode"
 	"github.com/loft-sh/devpod/pkg/ide/vscode"
+	"github.com/loft-sh/devpod/pkg/loft"
 	open2 "github.com/loft-sh/devpod/pkg/open"
 	"github.com/loft-sh/devpod/pkg/port"
 	provider2 "github.com/loft-sh/devpod/pkg/provider"
@@ -125,6 +127,13 @@ func NewUpCmd(flags *flags.GlobalFlags) *cobra.Command {
 				return err
 			}
 
+			if !cmd.Proxy {
+				err = checkProviderUpdate(devPodConfig, client.Provider(), logger)
+				if err != nil {
+					return err
+				}
+			}
+
 			return cmd.Run(ctx, devPodConfig, client, logger)
 		},
 	}
@@ -961,3 +970,62 @@ func performGpgForwarding(
 
 	return nil
 }
+
+// checkProviderUpdate currently only ensures the local provider is in sync with the remote for DevPod Pro instances
+// Potentially auto-upgrade other providers in the future.
+func checkProviderUpdate(devPodConfig *config.Config, providerName string, log log.Logger) error {
+	fmt.Printf("potentially update %s \n", providerName)
+	proInstances, err := workspace2.ListProInstances(devPodConfig, log)
+	if err != nil {
+		return fmt.Errorf("list pro instances: %w", err)
+	} else if len(proInstances) == 0 {
+		return nil
+	}
+
+	proInstance, ok := workspace2.FindProviderProInstance(proInstances, providerName)
+	if !ok {
+		return nil
+	}
+
+	// compare versions
+	newVersion, err := loft.GetProInstanceDevPodVersion(proInstance)
+	if err != nil {
+		return fmt.Errorf("version for pro instance %s: %w", proInstance.Host, err)
+	}
+
+	p, err := workspace2.FindProvider(devPodConfig, proInstance.Provider, log)
+	if err != nil {
+		return fmt.Errorf("get provider config for pro provider %s: %w", proInstance.Provider, err)
+	}
+	v1, err := semver.Parse(strings.TrimPrefix(newVersion, "v"))
+	if err != nil {
+		return fmt.Errorf("parse version %s: %w", newVersion, err)
+	}
+	v2, err := semver.Parse(strings.TrimPrefix(p.Config.Version, "v"))
+	if err != nil {
+		return fmt.Errorf("parse version %s: %w", p.Config.Version, err)
+	}
+	if v1.Compare(v2) == 0 {
+		return nil
+	}
+	log.Infof("New provider version available, attempting to update %s", proInstance.Provider)
+
+	providerSource, err := workspace2.ResolveProviderSource(devPodConfig, proInstance.Provider, log)
+	if err != nil {
+		return fmt.Errorf("resolve provider source %s: %w", proInstance.Provider, err)
+	}
+
+	splitted := strings.Split(providerSource, "@")
+	if len(splitted) == 0 {
+		return fmt.Errorf("no provider source found %s", providerSource)
+	}
+	providerSource = splitted[0] + "@" + newVersion
+
+	_, err = workspace2.UpdateProvider(devPodConfig, providerName, providerSource, log)
+	if err != nil {
+		return fmt.Errorf("update provider %s: %w", proInstance.Provider, err)
+	}
+
+	log.Donef("Successfully updated provider %s", proInstance.Provider)
+	return nil
+}
diff --git a/pkg/loft/version.go b/pkg/loft/version.go
new file mode 100644
index 000000000..f0fa02f2a
--- /dev/null
+++ b/pkg/loft/version.go
@@ -0,0 +1,51 @@
+package loft
+
+import (
+	"encoding/json"
+	"fmt"
+	"io"
+	"strings"
+
+	"github.com/loft-sh/devpod/pkg/http"
+	"github.com/loft-sh/devpod/pkg/provider"
+)
+
+type VersionObject struct {
+	// Version is the remote devpod version
+	DevPodVersion string `json:"devPodVersion,omitempty"`
+}
+
+func GetProInstanceDevPodVersion(proInstance *provider.ProInstance) (string, error) {
+	url := "https://" + proInstance.Host
+	return GetDevPodVersion(url)
+}
+
+func GetDevPodVersion(url string) (string, error) {
+	resp, err := http.GetHTTPClient().Get(url + "/version")
+	if err != nil {
+		return "", fmt.Errorf("get %s: %w", url, err)
+	} else if resp.StatusCode != 200 {
+		out, _ := io.ReadAll(resp.Body)
+		return "", fmt.Errorf("get %s: %s (Status: %d)", url, string(out), resp.StatusCode)
+	}
+
+	versionRaw, err := io.ReadAll(resp.Body)
+	if err != nil {
+		return "", fmt.Errorf("read %s: %w", url, err)
+	}
+
+	version := &VersionObject{}
+	err = json.Unmarshal(versionRaw, version)
+	if err != nil {
+		return "", fmt.Errorf("parse %s: %w", url, err)
+	} else if version.DevPodVersion == "" {
+		return "", fmt.Errorf("unexpected version '%s', please use --version to define a provider version", version.DevPodVersion)
+	}
+
+	// make sure it starts with a v
+	if !strings.HasPrefix(version.DevPodVersion, "v") {
+		version.DevPodVersion = "v" + version.DevPodVersion
+	}
+
+	return version.DevPodVersion, nil
+}
diff --git a/pkg/workspace/pro.go b/pkg/workspace/pro.go
index 663dc765d..7ce8dfe12 100644
--- a/pkg/workspace/pro.go
+++ b/pkg/workspace/pro.go
@@ -32,3 +32,13 @@ func ListProInstances(devPodConfig *config.Config, log log.Logger) ([]*provider2
 
 	return retProInstances, nil
 }
+
+func FindProviderProInstance(proInstances []*provider2.ProInstance, providerName string) (*provider2.ProInstance, bool) {
+	for _, instance := range proInstances {
+		if instance.Provider == providerName {
+			return instance, true
+		}
+	}
+
+	return nil, false
+}