Change:
return; // already initialized, token available } <del> return await this.progressService.withProgress( { location: ProgressLocation.Window, title: localize({ key: 'initialize.progress.title', comment: ['Only translate 'Looking for remote tunnel', do not change the format of the rest (markdown link format)'] }, "[Looking for remote tunnel](command:{0})", RemoteTunnelCommandIds.showLog), }, async (progress: IProgress<IProgressStep>) => { const listener = this.remoteTunnelService.onDidChangeTunnelStatus(status => { switch (status.type) { case 'connecting': if (status.progress) { progress.report({ message: status.progress }); } break; } }); let newSession: IRemoteTunnelSession | undefined; if (mode.active) { const token = await this.getSessionToken(mode.session); if (token) { newSession = { ...mode.session, token }; } </del> <ins> const doInitialStateDiscovery = async (progress?: IProgress<IProgressStep>) => { const listener = progress && this.remoteTunnelService.onDidChangeTunnelStatus(status => { switch (status.type) { case 'connecting': if (status.progress) { progress.report({ message: status.progress }); } break; </ins> } <del> const status = await this.remoteTunnelService.initialize(mode.active && newSession ? { ...mode, session: newSession } : INACTIVE_TUNNEL_MODE); listener.dispose(); if (status.type === 'connected') { this.connectionInfo = status.info; this.connectionStateContext.set('connected'); return; </del> <ins> }); let newSession: IRemoteTunnelSession | undefined; if (mode.active) { const token = await this.getSessionToken(mode.session); if (token) { newSession = { ...mode.session, token }; </ins> } } <del> ); </del> <ins> const status = await this.remoteTunnelService.initialize(mode.active && newSession ? { ...mode, session: newSession } : INACTIVE_TUNNEL_MODE); listener?.dispose(); if (status.type === 'connected') { this.connectionInfo = status.info; this.connectionStateContext.set('connected'); return; } }; const hasUsed = this.storageService.getBoolean(REMOTE_TUNNEL_HAS_USED_BEFORE, StorageScope.APPLICATION, false); if (hasUsed) { await this.progressService.withProgress( { location: ProgressLocation.Window, title: localize({ key: 'initialize.progress.title', comment: ['Only translate 'Looking for remote tunnel', do not change the format of the rest (markdown link format)'] }, "[Looking for remote tunnel](command:{0})", RemoteTunnelCommandIds.showLog), }, doInitialStateDiscovery ); } else { doInitialStateDiscovery(undefined); } </ins> } private getPreferredTokenFromSession(session: ExistingSessionItem) {

Discussion:
After starting up VS Code for the first time, something strange appears in the status bar: ! Click it. Then click the notification link. The output opens empty. Wait long enough and an error comes up: !
The "syntax error" will log the output, so if you see that again, please share more details what do you think about not showing the "Looking for tunnel" progress on startup? Most users don't use remote tunnels, so this is just noise.
I think user only see that if they turned on Remote Tunnel Access. Yes, I guess we can remove it.
It looks like that progress is shown whenever the RemoteTunnelWorkbenchContribution is instantiated unless there's already a known session.