fix: improve confusing update messaging (#1682)

<img width="1790" height="342" alt="image (1)"
src="https://github.com/user-attachments/assets/1ae33b52-aadd-4975-8573-a2cbcd9c24ab"
/>

The CLI confusingly displays two conflicting messages - this is because
in the logic for displaying the message "Running with latest Speakeasy
version" which is based on looking at the workflow.yaml
`speakeasyVersion: latest` value, we do not actually check that we are
on latest before rendering it (you can see from the subsequent
screenshot that we do eventually autoupgrade)

Author: adaam2

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

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 {