diff --git a/src/patcher/paragraph-split-inject.spec.ts b/src/patcher/paragraph-split-inject.spec.ts
index 7b30dd36ade..b2eda0ddd2b 100644
--- a/src/patcher/paragraph-split-inject.spec.ts
+++ b/src/patcher/paragraph-split-inject.spec.ts
@@ -228,8 +228,15 @@ describe("paragraph-split-inject", () => {
                 "*",
             );
 
+            // When the token is not found in the text, splitIndex remains -1
+            // so left gets nothing and right gets all elements
             expect(output).to.deep.equal({
                 left: {
+                    elements: [],
+                    name: "w:r",
+                    type: "element",
+                },
+                right: {
                     elements: [
                         {
                             attributes: {
@@ -243,11 +250,6 @@ describe("paragraph-split-inject", () => {
                     name: "w:r",
                     type: "element",
                 },
-                right: {
-                    elements: [],
-                    name: "w:r",
-                    type: "element",
-                },
             });
         });
 
diff --git a/src/patcher/paragraph-split-inject.ts b/src/patcher/paragraph-split-inject.ts
index c3033732cdc..56c1bae85ec 100644
--- a/src/patcher/paragraph-split-inject.ts
+++ b/src/patcher/paragraph-split-inject.ts
@@ -24,11 +24,16 @@ export const findRunElementIndexWithToken = (paragraphElement: Element, token: s
 };
 
 export const splitRunElement = (runElement: Element, token: string): { readonly left: Element; readonly right: Element } => {
-    let splitIndex = 0;
+    let splitIndex = -1;
 
     const splitElements =
         runElement.elements
             ?.map((e, i) => {
+                // Only take the first split we see, don't mutate the rest
+                if (splitIndex !== -1) {
+                    return e;
+                }
+
                 if (e.type === "element" && e.name === "w:t") {
                     const text = (e.elements?.[0]?.text as string) ?? "";
                     const splitText = text.split(token);
@@ -37,7 +42,12 @@ export const splitRunElement = (runElement: Element, token: string): { readonly
                         ...patchSpaceAttribute(e),
                         elements: createTextElementContents(t),
                     }));
-                    splitIndex = i;
+
+                    // Only set splitIndex if this element actually contains the token
+                    if (splitText.length > 1) {
+                        splitIndex = i;
+                    }
+
                     return newElements;
                 } else {
                     return e;
diff --git a/src/patcher/paragraph-token-replacer.ts b/src/patcher/paragraph-token-replacer.ts
index 32eec3bbcc4..1fd45c307fa 100644
--- a/src/patcher/paragraph-token-replacer.ts
+++ b/src/patcher/paragraph-token-replacer.ts
@@ -29,7 +29,7 @@ export const replaceTokenInParagraphElement = ({
         for (const { text, index, start, end } of run.parts) {
             switch (replaceMode) {
                 case ReplaceMode.START:
-                    if (startIndex >= start) {
+                    if (startIndex >= start && startIndex <= end) {
                         const offsetStartIndex = startIndex - start;
                         const offsetEndIndex = Math.min(endIndex, end) - start;
                         const partToReplace = run.text.substring(offsetStartIndex, offsetEndIndex + 1);
diff --git a/src/patcher/replacer.spec.ts b/src/patcher/replacer.spec.ts
index 762c9403225..be3fb64e022 100644
--- a/src/patcher/replacer.spec.ts
+++ b/src/patcher/replacer.spec.ts
@@ -6,6 +6,7 @@ import { Paragraph, TextRun } from "@file/paragraph";
 
 import { PatchType } from "./from-docx";
 import { replacer } from "./replacer";
+import { traverse } from "./traverser";
 
 export const MOCK_JSON = {
     elements: [
@@ -724,5 +725,71 @@ describe("replacer", () => {
             expect(JSON.stringify(element)).not.to.contain("{{empty}}");
             expect(didFindOccurrence).toBe(true);
         });
+
+        it("should handle multiple replacements in a single run with multiple text elements", () => {
+            // Minimal reproduction of bug where:
+            // 1. A w:r (run) contains multiple w:t (text) elements
+            // 2. First replacement splits the run, creating additional w:t elements
+            // 3. Second replacement must correctly:
+            //    - Find the token in the remaining w:t elements (not get confused by earlier parts)
+            //    - Split at the correct position in the flattened element array
+            const json = {
+                elements: [
+                    {
+                        type: "element",
+                        name: "w:p",
+                        elements: [
+                            {
+                                type: "element",
+                                name: "w:r",
+                                elements: [
+                                    {
+                                        type: "element",
+                                        name: "w:t",
+                                        elements: [{ type: "text", text: "A{{token1}}B" }],
+                                    },
+                                    { type: "element", name: "w:tab" },
+                                    {
+                                        type: "element",
+                                        name: "w:t",
+                                        elements: [{ type: "text", text: "C{{token2}}D" }],
+                                    },
+                                ],
+                            },
+                        ],
+                    },
+                ],
+            };
+
+            // First replacement
+            replacer({
+                json,
+                patch: { type: PatchType.PARAGRAPH, children: [new TextRun("X")] },
+                patchText: "{{token1}}",
+                context: {
+                    file: {} as unknown as File,
+                    viewWrapper: { Relationships: {} } as unknown as IViewWrapper,
+                    stack: [],
+                },
+            });
+
+            // Second replacement - this is where the bug occurred
+            const { didFindOccurrence } = replacer({
+                json,
+                patch: { type: PatchType.PARAGRAPH, children: [new TextRun("Y")] },
+                patchText: "{{token2}}",
+                context: {
+                    file: {} as unknown as File,
+                    viewWrapper: { Relationships: {} } as unknown as IViewWrapper,
+                    stack: [],
+                },
+            });
+
+            expect(didFindOccurrence).toBe(true);
+
+            // Verify the rendered text is correct
+            const paragraphs = traverse(json);
+            expect(paragraphs[0].text).to.equal("AXBCYD");
+        });
     });
 });