diff --git a/internal/actions/runWorkflow.go b/internal/actions/runWorkflow.go
index 7c495d84..d7ad93ff 100644
--- a/internal/actions/runWorkflow.go
+++ b/internal/actions/runWorkflow.go
@@ -33,7 +33,7 @@ func RunWorkflow() error {
 			return err
 		}
 
-		return runWorkflow(g, resolvedVersion)
+		return runWorkflow(g, resolvedVersion, false)
 	}
 
 	pinnedVersion := wf.SpeakeasyVersion.String()
@@ -53,7 +53,7 @@ func RunWorkflow() error {
 		logging.Info("Attempting auto-upgrade from Speakeasy version %s to %s", pinnedVersion, resolvedVersion)
 	}
 
-	err = runWorkflow(g, resolvedVersion)
+	err = runWorkflow(g, resolvedVersion, true)
 	if attemptingAutoUpgrade {
 		// If we tried to upgrade and the run succeeded, update the workflow file with the new version
 		if err == nil {
@@ -68,19 +68,24 @@ func RunWorkflow() error {
 			logging.Info("Error running workflow with version %s: %v", firstRunVersion, err)
 			logging.Info("Trying again with pinned version %s", pinnedVersion)
 
+			// Before re-running, reset anything we already did
+			if err := g.HardResetToDefault(); err != nil {
+				return err
+			}
+
 			resolvedVersion, err := cli.Download(firstRunVersion, g)
 			if err != nil {
 				return err
 			}
 
-			return runWorkflow(g, resolvedVersion)
+			return runWorkflow(g, resolvedVersion, false)
 		}
 	}
 
 	return err
 }
 
-func runWorkflow(g *git.Git, resolvedVersion string) error {
+func runWorkflow(g *git.Git, resolvedVersion string, forceFail bool) error {
 	wf, _, err := configuration.GetWorkflowAndValidateLanguages(true)
 	if err != nil {
 		return err
@@ -195,6 +200,10 @@ func runWorkflow(g *git.Git, resolvedVersion string) error {
 		return err
 	}
 
+	if forceFail {
+		return fmt.Errorf("force fail")
+	}
+
 	success = true
 
 	return nil
diff --git a/internal/git/git.go b/internal/git/git.go
index ccfb6a3b..cf9a5cd7 100644
--- a/internal/git/git.go
+++ b/internal/git/git.go
@@ -33,9 +33,10 @@ import (
 )
 
 type Git struct {
-	accessToken string
-	repo        *git.Repository
-	client      *github.Client
+	accessToken    string
+	repo           *git.Repository
+	client         *github.Client
+	defaultBreanch string
 }
 
 func New(accessToken string) *Git {
@@ -85,6 +86,13 @@ func (g *Git) CloneRepo() error {
 	}
 	g.repo = r
 
+	defaultBranch, err := g.GetCurrentBranch()
+	if err != nil {
+		// Swallow this error for now. Functionality will be unchanged from previous behavior if it fails
+		logging.Info("failed to get default branch: %s", err.Error())
+	}
+	g.defaultBreanch = defaultBranch
+
 	return nil
 }
 
@@ -236,6 +244,11 @@ func (g *Git) FindAndCheckoutBranch(branchName string) (string, error) {
 	return branchName, nil
 }
 
+func (g *Git) HardResetToDefault() error {
+	origin := fmt.Sprintf("origin/%s", g.defaultBreanch)
+	return g.Reset("--hard", origin)
+}
+
 func (g *Git) Reset(args ...string) error {
 	// We execute this manually because go-git doesn't support all the options we need
 	args = append([]string{"reset"}, args...)
@@ -264,24 +277,12 @@ func (g *Git) FindOrCreateBranch(branchName string, action environment.Action) (
 	}
 
 	if branchName != "" {
-		defaultBranch, err := g.GetCurrentBranch()
-		if err != nil {
-			// Swallow this error for now. Functionality will be unchanged from previous behavior if it fails
-			logging.Info("failed to get default branch: %s", err.Error())
-		}
-
 		branchName, err := g.FindAndCheckoutBranch(branchName)
 		if err != nil {
 			return "", err
 		}
 
-		origin := fmt.Sprintf("origin/%s", defaultBranch)
-		if err = g.Reset("--hard", origin); err != nil {
-			// Swallow this error for now. Functionality will be unchanged from previous behavior if it fails
-			logging.Info("failed to reset branch: %s", err.Error())
-		}
-
-		return branchName, nil
+		return branchName, g.HardResetToDefault()
 	}
 
 	if action == environment.ActionRunWorkflow {