diff --git a/web/src/test/auto/headless/engine/predictive-text/templates/tokenization.tests.ts b/web/src/test/auto/headless/engine/predictive-text/templates/tokenization.tests.ts
index 3bc636c412..0aa4f9551e 100644
--- a/web/src/test/auto/headless/engine/predictive-text/templates/tokenization.tests.ts
+++ b/web/src/test/auto/headless/engine/predictive-text/templates/tokenization.tests.ts
@@ -175,7 +175,7 @@ describe('Tokenization functions', function() {
     });
 
     it('properly handles empty-context cases', function() {
-      // Wordbreaking on a empty space => no word.
+      // Wordbreaking on a empty space => no word, but empty initial token.
       let context = {
         left: '', startOfBuffer: true,
         right: '', endOfBuffer: true
@@ -184,7 +184,7 @@ describe('Tokenization functions', function() {
       let tokenization = models.tokenize(wordBreakers.default, context);
 
       let expectedResult: models.Tokenization = {
-        left: [],
+        left: [{text: '', isWhitespace: false}],
         right: [],
         caretSplitsToken: false
       };
@@ -193,11 +193,11 @@ describe('Tokenization functions', function() {
     });
 
     it('properly handles null context cases', function() {
-      // Wordbreaking on a empty space => no word.
+      // Wordbreaking on a empty space => no word, but empty initial token.
       let tokenization = models.tokenize(wordBreakers.default, null);
 
       let expectedResult: models.Tokenization = {
-        left: [],
+        left: [{text: '', isWhitespace: false}],
         right: [],
         caretSplitsToken: false
       };
diff --git a/web/src/test/auto/headless/engine/predictive-text/worker-thread/worker-custom-punctuation.tests.ts b/web/src/test/auto/headless/engine/predictive-text/worker-thread/worker-custom-punctuation.tests.ts
index cd4dbd106e..01f1a6ac96 100644
--- a/web/src/test/auto/headless/engine/predictive-text/worker-thread/worker-custom-punctuation.tests.ts
+++ b/web/src/test/auto/headless/engine/predictive-text/worker-thread/worker-custom-punctuation.tests.ts
@@ -87,17 +87,30 @@ describe('Custom Punctuation', function () {
         // the tests run smoothly.
         wordbreaker: (text) => {
           const textLen = text.length;
-          if(text.charAt(textLen - 1) == " ") {
-            return [
-              {text: text.substring(0, 1), start: 0, end: 1, length: 1},
-              {text: text.substring(1, textLen-2), start: 1, end: textLen-1, length: textLen-2},
-              {text: text.substring(textLen-1), start: textLen-1, end: textLen, length: 1}
-            ];
+          if(text.charAt(0) == "᚛") { // ensure the prior token component (the '᚛') wordbreaks.
+            if(text.charAt(textLen - 1) == " ") { // ensure the insert-after component word-breaks.
+              return [
+                {text: text.substring(0, 1), start: 0, end: 1, length: 1},
+                {text: text.substring(1, textLen-2), start: 1, end: textLen-1, length: textLen-2},
+                {text: text.substring(textLen-1), start: textLen-1, end: textLen, length: 1}
+              ];
+            } else {
+              return [
+                {text: text.substring(0, 1), start: 0, end: 1, length: 1},
+                {text: text.substring(1), start: 1, end: textLen, length: textLen-1}
+              ];
+            }
           } else {
-            return [
-              {text: text.substring(0, 1), start: 0, end: 1, length: 1},
-              {text: text.substring(1), start: 1, end: textLen, length: textLen-1}
-            ];
+            if(text.charAt(textLen - 1) == " ") {
+              return [
+                {text: text.substring(0, textLen-2), start: 0, end: textLen-1, length: textLen-1},
+                {text: text.substring(textLen-1), start: textLen-1, end: textLen, length: 1}
+              ];
+            } else {
+              return [
+                {text: text, start: 0, end: textLen, length: textLen}
+              ];
+            }
           }
         }
       });