diff --git a/changelogs/fragments/10901.yml b/changelogs/fragments/10901.yml
new file mode 100644
index 000000000000..5272b60dda7d
--- /dev/null
+++ b/changelogs/fragments/10901.yml
@@ -0,0 +1,2 @@
+fix:
+- First character being trimmed during Query Snippet Insertion ([#10901](https://github.com/opensearch-project/OpenSearch-Dashboards/pull/10901))
\ No newline at end of file
diff --git a/src/plugins/data/public/query_snippet_suggestions/ppl/suggestions.test.ts b/src/plugins/data/public/query_snippet_suggestions/ppl/suggestions.test.ts
index 0131c3ad1d3e..ebb46a50a60b 100644
--- a/src/plugins/data/public/query_snippet_suggestions/ppl/suggestions.test.ts
+++ b/src/plugins/data/public/query_snippet_suggestions/ppl/suggestions.test.ts
@@ -79,8 +79,8 @@ describe('PPL Query Snippet Suggestions', () => {
   });
 
   describe('convertQueryToMonacoSuggestion', () => {
-    it('should convert queries to Monaco suggestions without user query', () => {
-      const result = convertQueryToMonacoSuggestion(mockQueries, '');
+    it('should convert queries to Monaco suggestions', () => {
+      const result = convertQueryToMonacoSuggestion(mockQueries);
 
       expect(result).toHaveLength(9); // 3 queries with 3, 3, 3 segments each
 
@@ -98,8 +98,8 @@ describe('PPL Query Snippet Suggestions', () => {
       );
     });
 
-    it('should convert queries to Monaco suggestions with user query', () => {
-      const result = convertQueryToMonacoSuggestion(mockQueries, 'source = logs | ');
+    it('should not include insertText in base conversion', () => {
+      const result = convertQueryToMonacoSuggestion(mockQueries);
 
       expect(result).toHaveLength(9);
 
@@ -122,7 +122,7 @@ describe('PPL Query Snippet Suggestions', () => {
         },
       ];
 
-      const result = convertQueryToMonacoSuggestion(duplicateQueries, '');
+      const result = convertQueryToMonacoSuggestion(duplicateQueries);
 
       // Should only have 2 unique suggestions (source = logs, where status = "error")
       expect(result).toHaveLength(2);
@@ -142,7 +142,7 @@ describe('PPL Query Snippet Suggestions', () => {
 
       const whereResult = result.find((s) => s.text.startsWith('where'));
       expect(whereResult).toBeDefined();
-      expect(whereResult?.insertText).toBe('re status = "error" '); // Should complete "whe" to "where status = "error"" with trailing space
+      expect(whereResult?.insertText).toBe('where status = "error" '); // Should complete "whe" to "where status = "error"" with trailing space
     });
 
     it('should return empty array when no matching suggestions', async () => {
@@ -158,7 +158,7 @@ describe('PPL Query Snippet Suggestions', () => {
 
       const statsResult = result.find((s) => s.text.startsWith('stats'));
       expect(statsResult).toBeDefined();
-      expect(statsResult?.insertText).toBe('ats count() by host ');
+      expect(statsResult?.insertText).toBe('stats count() by host ');
     });
 
     it('should not return suggestions that match exactly', async () => {
@@ -190,5 +190,79 @@ describe('PPL Query Snippet Suggestions', () => {
 
       expect(result).toHaveLength(0);
     });
+
+    describe('token-based insertText logic', () => {
+      it('should handle partial token matching correctly', async () => {
+        const result = await getPPLQuerySnippetForSuggestions('source = logs | wh');
+
+        const whereResult = result.find((s) => s.text.startsWith('where'));
+        expect(whereResult).toBeDefined();
+        expect(whereResult?.insertText).toBe('where status = "error" ');
+      });
+
+      it('should skip fully matched tokens and insert remaining tokens', async () => {
+        const result = await getPPLQuerySnippetForSuggestions('source = logs | where status');
+
+        const whereResult = result.find((s) => s.text.startsWith('where'));
+        expect(whereResult).toBeDefined();
+        expect(whereResult?.insertText).toBe('= "error" ');
+      });
+
+      it('should handle multiple fully matched tokens', async () => {
+        const result = await getPPLQuerySnippetForSuggestions('source = logs | where status =');
+
+        const whereResult = result.find((s) => s.text.startsWith('where'));
+        expect(whereResult).toBeDefined();
+        expect(whereResult?.insertText).toBe('"error" ');
+      });
+
+      it('should return complete suggestion when no tokens match', async () => {
+        const result = await getPPLQuerySnippetForSuggestions('source = logs | xyz');
+
+        expect(result).toHaveLength(0); // No suggestions should match 'xyz'
+      });
+
+      it('should handle case-insensitive token matching', async () => {
+        const result = await getPPLQuerySnippetForSuggestions('source = logs | WHERE STATUS');
+
+        const whereResult = result.find((s) => s.text.startsWith('where'));
+        expect(whereResult).toBeDefined();
+        expect(whereResult?.insertText).toBe('= "error" ');
+      });
+
+      it('should handle single character partial match', async () => {
+        const result = await getPPLQuerySnippetForSuggestions('source = logs | w');
+
+        const whereResult = result.find((s) => s.text.startsWith('where'));
+        expect(whereResult).toBeDefined();
+        expect(whereResult?.insertText).toBe('where status = "error" ');
+      });
+
+      it('should handle exact token boundary matching', async () => {
+        const result = await getPPLQuerySnippetForSuggestions('source = logs | where');
+
+        const whereResult = result.find((s) => s.text.startsWith('where'));
+        expect(whereResult).toBeDefined();
+        expect(whereResult?.insertText).toBe('status = "error" ');
+      });
+
+      it('should handle suggestions with different token structures', async () => {
+        const result = await getPPLQuerySnippetForSuggestions('source = metrics | f');
+
+        const fieldsResult = result.find((s) => s.text.startsWith('fields'));
+        expect(fieldsResult).toBeDefined();
+        expect(fieldsResult?.insertText).toBe('fields timestamp, cpu_usage ');
+      });
+
+      it('should handle when suggestion has fewer tokens than user input', async () => {
+        // Test with a complex user query that has more tokens than any single suggestion
+        const result = await getPPLQuerySnippetForSuggestions(
+          'source = logs | where status = "error" extra token'
+        );
+
+        // Should have no matches since no suggestion starts with this complex pattern
+        expect(result).toHaveLength(0);
+      });
+    });
   });
 });
diff --git a/src/plugins/data/public/query_snippet_suggestions/ppl/suggestions.ts b/src/plugins/data/public/query_snippet_suggestions/ppl/suggestions.ts
index 76c50fdc2f8a..ae1498e24e0d 100644
--- a/src/plugins/data/public/query_snippet_suggestions/ppl/suggestions.ts
+++ b/src/plugins/data/public/query_snippet_suggestions/ppl/suggestions.ts
@@ -16,10 +16,7 @@ export const extractSnippetsFromQuery = (query: string) => {
   return pplQuerySegments;
 };
 
-export const convertQueryToMonacoSuggestion = (
-  queries: QuerySnippetItem[],
-  userQuery: string
-): QuerySuggestion[] => {
+export const convertQueryToMonacoSuggestion = (queries: QuerySnippetItem[]): QuerySuggestion[] => {
   const textMap = new Map<string, QuerySuggestion>();
 
   queries.forEach((query) => {
@@ -52,11 +49,12 @@ export const getPPLQuerySnippetForSuggestions = async (
   // Fetfch all User Queries
   const userQueries = await getUserPastQueries(languageId);
 
-  const suggestions = convertQueryToMonacoSuggestion(userQueries, userQuery);
+  const suggestions = convertQueryToMonacoSuggestion(userQueries);
 
   // Extract the last Segment from the query
   const userQuerySegments = userQuery.split('|');
   const currentUserQuerySegment = userQuerySegments.pop()?.trim().toLowerCase();
+  const typedTokens = currentUserQuerySegment?.split(/\s+/);
 
   // Using currentUserQuery to do a prefix filtering of the Query Segments
   if (currentUserQuerySegment) {
@@ -67,10 +65,29 @@ export const getPPLQuerySnippetForSuggestions = async (
           currentUserQuerySegment !== suggestion.text
         );
       })
-      .map((suggestion) => ({
-        ...suggestion,
-        insertText: suggestion.text.slice(currentUserQuerySegment.length).trim() + ' ',
-      }));
+      .map((suggestion) => {
+        const suggestionTokens = suggestion.text.split(/\s+/);
+
+        let insertIndex = 0;
+
+        // Skip fully matched tokens only
+        while (
+          typedTokens &&
+          insertIndex < typedTokens.length &&
+          insertIndex < suggestionTokens.length &&
+          suggestionTokens[insertIndex].toLowerCase() === typedTokens[insertIndex].toLowerCase()
+        ) {
+          insertIndex++;
+        }
+
+        // Insert from the first partially matched token onwards
+        const remainingTokens = suggestionTokens.slice(insertIndex).join(' ');
+
+        return {
+          ...suggestion,
+          insertText: remainingTokens + ' ',
+        };
+      });
   }
 
   return [];