If the condition is false, Alert and Cancel

I can’t figure out how to properly make an alert for myself that a RegEx query is false because the text is not in the content. See the first alert condition. I assume I have to repeat this for every RegEx search and then at the end, if at least one is missing, tell Drafts, not to insert text. Am I on the right track?

//Date of Assessment

let matchDateAssessment = draft.content.match(/Date\sof\sAssessment:\s(\w+\s\d{1,2}\,\s\d{4})/);

if (matchDateAssessment)	{
	var dateAssessment = draft.content.match(/Date\sof\sAssessment:\s(\w+\s\d{1,2}\,\s\d{4})/)[1]
} 	else {
	alert('Missing Date of Assessment'); context.fail();


let matchDiagnosis = draft.content.match(/(F\d{1,2}\.\d{1,2}\s.+)\./);

if (matchDiagnosis)	{
var diagnosis = draft.content.match(/(F\d{1,2}\.\d{1,2}\s.+)\./)[1];
} 	else {
	alert('Missing Diagnosis'); context.fail();

//First Session

let matchFirstSession = draft.content.match(/\d\/\d{1,2}\s\-\s(\w+\s\d+\,\s\d+)/);

if (matchFirstSession)	{
var firstSession = draft.content.match(/\d\/\d{1,2}\s\-\s(\w+\s\d+\,\s\d+)/)[1];
} 	else {
	alert('Missing Date of First Session'); context.fail();

//Number of Sessions

let matchSessions = draft.content.match(/TP\d{1,2}:\s(\d+)/);

if (matchSessions)	{
var sessions = draft.content.match(/TP\d{1,2}:\s(\d+)/)[1];
} 	else {
	alert('Missing Number of Session'); context.fail();

//Treatment Plan Number

let matchTreatmentPlan = draft.content.match(/TP(\d)/);

if (matchTreatmentPlan)	{
var treatmentPlan = draft.content.match(/TP(\d)/)[1];

//Funciton - Convert numebrs to words

function numeral(number){
   var numbers = ['zero','first','second','third','fourth','fifth','sixth','seventh','eighth'];
   return numbers[number]

treatmentPlan = numeral(treatmentPlan);

} 	else {
	alert('Missing Treatment Plan Number'); context.fail();

//Insert Text if all RegEx queries were found

if ((dateAssessment) && (diagnosis) && (firstSession) && (sessions) && (treatmentPlan))	{

	editor.setSelectedText(`Mr. XX's initial psychological assessment was completed on ${dateAssessment}. His initial presentation was consistent with the DSM-5 and ICD-10 diagnoses of ${diagnosis}. Mr. XX initiated his *${treatmentPlan} psychotherapy treatment plan* on ${firstSession}, and has completed all ${sessions} of his cognitive-behavioural therapy sessions.`);
	}	else	{

You probably want a loop construct, and some objects to hold your regexes and results. Something like:

let expressions = {
  dateAssessment: /Date\sof\sAssessment:\s(\w+\s\d{1,2}\,\s\d{4})/,
  matchDiagnosis: /(F\d{1,2}\.\d{1,2}\s.+)\./,
  // etc...

let results = { }; // empty object to hold results
let didFail = false;

// loop over each key in the expressions object
for(let key of Object.keys(expressions)) {
  let re = expressions[key]; // get the regex
  let result = draft.content.match(re);
  if (result) {
    results[key] = result[1];
  else {
    didFail = true; // was not found!

// if !didFail, then every test found something 
if (!didFail) {
  // insert the text
  // the matches will can be accessed like: results["dateAssessment"], etc.