diff --git a/src/views/components/AddTaskModal.jsx b/src/views/components/AddTaskModal.jsx
index f886be5..806a897 100644
--- a/src/views/components/AddTaskModal.jsx
+++ b/src/views/components/AddTaskModal.jsx
@@ -416,15 +416,6 @@ const TaskInput = ({ autoFocus, onChoreUpdate, isModalOpen, onClose }) => {
         dueDateHighlight = dueDateParsed.highlight[0]
       }
 
-      if (repeat.result) {
-        // if repeat has result the cleaned sentence will remove the date related info which mean
-        // we need to reparse the date again to get the correct due date:
-        const dueDateParsedAgain = parseDueDate(sentence, chrono)
-        if (dueDateParsedAgain.result) {
-          syncDueDateStates(dueDateParsedAgain.result)
-        }
-      }
-
       // Create the cleaned sentence by sequentially applying all cleanups
       let cleanedSentence = sentence
       if (priority.result) cleanedSentence = priority.cleanedSentence
diff --git a/src/views/components/CustomParsers.js b/src/views/components/CustomParsers.js
index 7d5d689..8e5cb4e 100644
--- a/src/views/components/CustomParsers.js
+++ b/src/views/components/CustomParsers.js
@@ -45,6 +45,20 @@ const ALL_MONTHS = Object.values(VALID_MONTHS).filter(
   (v, i, a) => a.indexOf(v) === i,
 )
 
+// Helper function to validate word boundaries for date/time matches
+// Prevents matching partial words like 'wed' in 'wedding', 'fri' in 'friend', etc.
+const isValidWordBoundary = (text, matchIndex, matchLength) => {
+  const charBefore = matchIndex > 0 ? text[matchIndex - 1] : ' '
+  const charAfter =
+    matchIndex + matchLength < text.length
+      ? text[matchIndex + matchLength]
+      : ' '
+  // Valid boundaries: spaces, punctuation, but NOT alphanumeric or word-forming characters
+  return !(
+    /[\p{L}\p{N}_]/u.test(charBefore) || /[\p{L}\p{N}_]/u.test(charAfter)
+  )
+}
+
 export const parsePriority = inputSentence => {
   let sentence = inputSentence.toLowerCase()
   const priorityMap = {
@@ -292,7 +306,22 @@ export const parseRepeatV2 = inputSentence => {
           .toLowerCase()
           .split(/ and |,|\s/)
           .map(day => day.trim())
-          .filter(day => VALID_DAYS[day])
+          .filter(day => {
+            // Validate that the day abbreviation is at proper word boundaries
+            // This prevents matches like 'wed' in 'wedding', 'fri' in 'friend'
+            if (!VALID_DAYS[day]) return false
+            // For short abbreviations (3 chars or less), validate word boundaries
+            if (day.length <= 3) {
+              const dayIndex = sentence.toLowerCase().indexOf(day)
+              if (dayIndex === -1) return false
+              return isValidWordBoundary(
+                sentence.toLowerCase(),
+                dayIndex,
+                day.length,
+              )
+            }
+            return true
+          })
           .map(day => VALID_DAYS[day])
         if (!result.frequencyMetadata.days.length)
           return { result: null, name: null, cleanedSentence: inputSentence }
@@ -318,7 +347,20 @@ export const parseRepeatV2 = inputSentence => {
           .toLowerCase()
           .split(/ and |,|\s/)
           .map(month => month.trim())
-          .filter(month => VALID_MONTHS[month])
+          .filter(month => {
+            if (!VALID_MONTHS[month]) return false
+            // For short abbreviations (3 chars or less), validate word boundaries
+            if (month.length <= 3) {
+              const monthIndex = sentence.toLowerCase().indexOf(month)
+              if (monthIndex === -1) return false
+              return isValidWordBoundary(
+                sentence.toLowerCase(),
+                monthIndex,
+                month.length,
+              )
+            }
+            return true
+          })
           .map(month => VALID_MONTHS[month])
         result.frequencyMetadata.unit = 'days'
         return {
@@ -664,7 +706,7 @@ export const parseDueDate = (inputSentence, chrono) => {
     forwardDate: true,
   })
 
-  if (!parsedDueDate[0] || parsedDueDate[0].index === -1) {
+  if (!parsedDueDate.length) {
     return {
       result: null,
       highlight: [],
@@ -672,23 +714,15 @@ export const parseDueDate = (inputSentence, chrono) => {
     }
   }
 
-  let dueDateMatch = parsedDueDate[0]
+  // Select the first valid word-bounded date match
+  // Prevents false positives like "wed" in "wedding" while still allowing later valid matches
+  const dueDateMatch = parsedDueDate.find(
+    match =>
+      match.index !== -1 &&
+      isValidWordBoundary(inputSentence, match.index, match.text.length),
+  )
 
-  // Validate word boundaries for the matched date text
-  // This prevents matching partial words like "wed" in "wedding", fri in "friend", etc.
-  const matchStart = dueDateMatch.index
-  const matchEnd = matchStart + dueDateMatch.text.length
-
-  const charBefore = matchStart > 0 ? inputSentence[matchStart - 1] : ' '
-  const charAfter =
-    matchEnd < inputSentence.length ? inputSentence[matchEnd] : ' '
-
-  // Check if the match is part of a larger word
-  // If alphanumeric characters exist before/after, it's not a word boundary
-  const isValidWordBoundary =
-    !/[a-zA-Z0-9]/.test(charBefore) && !/[a-zA-Z0-9]/.test(charAfter)
-
-  if (!isValidWordBoundary) {
+  if (!dueDateMatch) {
     return {
       result: null,
       highlight: [],