diff --git a/cmd/root.go b/cmd/root.go
index 7954b81c4..08272ab05 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -161,6 +161,13 @@ func checkForUpdate(ctx context.Context, currentVersion, artifactArch string, cm
 		return
 	}
 
+	wf, _, _ := utils.GetWorkflow()
+
+	// If we are running the run command and a workflow file is present and specifies that the speakeasyVersion is "latest", don't display update notifications as it will be automatically updated when the command is run.
+	if cmd.Name() == "run" && wf != nil && wf.SpeakeasyVersion.String() == "latest" {
+		return
+	}
+
 	newerVersion, err := updates.GetNewerVersion(ctx, artifactArch, currentVersion)
 	if err != nil {
 		return // Don't display error to user
diff --git a/internal/model/command.go b/internal/model/command.go
index fc41cb2a8..a932f00d9 100644
--- a/internal/model/command.go
+++ b/internal/model/command.go
@@ -312,7 +312,11 @@ func runWithVersionFromWorkflowFile(cmd *cobra.Command) error {
 		}
 		desiredVersion = latest.String()
 
-		logger.PrintfStyled(styles.DimmedItalic, "Running with latest Speakeasy version\n")
+		// Check if we're actually running the latest version
+		currentVersion := events.GetSpeakeasyVersionFromContext(ctx)
+		if newerVersion, err := updates.GetNewerVersion(ctx, artifactArch, currentVersion); err == nil && newerVersion == nil {
+			logger.PrintfStyled(styles.DimmedItalic, "Running with latest Speakeasy version\n")
+		}
 	} else if desiredVersion == "pinned" {
 		return ErrPinned
 	} else {