diff --git a/plugin/src/database/database.ts b/plugin/src/database/database.ts
index d95f1fb..05f1e16 100644
--- a/plugin/src/database/database.ts
+++ b/plugin/src/database/database.ts
@@ -90,14 +90,17 @@ export class Database {
 		relativePath,
 		documentId,
 		parentVersionId,
+		hash,
 	}: {
 		relativePath: RelativePath;
 		documentId: DocumentId;
 		parentVersionId: DocumentVersionId;
+		hash: string;
 	}): Promise<void> {
 		this._documents.set(relativePath, {
 			documentId,
 			parentVersionId,
+			hash,
 		});
 		await this.save();
 	}
@@ -107,16 +110,19 @@ export class Database {
 		relativePath,
 		documentId,
 		parentVersionId,
+		hash,
 	}: {
 		oldRelativePath: RelativePath;
 		relativePath: RelativePath;
 		documentId: DocumentId;
 		parentVersionId: DocumentVersionId;
+		hash: string;
 	}): Promise<void> {
 		this._documents.delete(oldRelativePath);
 		this._documents.set(relativePath, {
 			documentId,
 			parentVersionId,
+			hash,
 		});
 		await this.save();
 	}
diff --git a/plugin/src/database/document-metadata.ts b/plugin/src/database/document-metadata.ts
index 1166797..b015d83 100644
--- a/plugin/src/database/document-metadata.ts
+++ b/plugin/src/database/document-metadata.ts
@@ -5,4 +5,5 @@ export type RelativePath = string;
 export interface DocumentMetadata {
 	documentId: DocumentId;
 	parentVersionId: DocumentVersionId;
+	hash: string;
 }
diff --git a/plugin/src/services/sync_service.ts b/plugin/src/services/sync_service.ts
index fc4c808..2a39485 100644
--- a/plugin/src/services/sync_service.ts
+++ b/plugin/src/services/sync_service.ts
@@ -1,4 +1,4 @@
-import * as plugin from "../../../backend/sync_lib/pkg/sync_lib.js";
+import * as lib from "../../../backend/sync_lib/pkg/sync_lib.js";
 
 import createClient, { Client } from "openapi-fetch";
 import type { components, paths } from "./types"; // generated by openapi-typescript
@@ -48,14 +48,13 @@ export class SyncServer {
 
 	public async create({
 		relativePath,
-		content,
+		contentBytes,
 		createdDate,
 	}: {
-		content: ArrayBuffer;
+		contentBytes: Uint8Array;
 		relativePath: string;
 		createdDate: Date;
 	}): Promise<components["schemas"]["DocumentVersion"]> {
-		let contentBytes = new Uint8Array(content);
 		let response = await this.client.POST("/vaults/{vault_id}/documents", {
 			params: {
 				path: { vault_id: SyncServer.VAULT_ID },
@@ -65,9 +64,8 @@ export class SyncServer {
 				},
 			},
 			body: {
-				contentBase64: plugin.bytes_to_base64(contentBytes),
+				contentBase64: lib.bytes_to_base64(contentBytes),
 				createdDate: createdDate.toISOString(),
-				isBinary: plugin.is_binary(contentBytes),
 				relativePath,
 			},
 		});
@@ -87,17 +85,15 @@ export class SyncServer {
 		documentId,
 		parentVersionId,
 		relativePath,
-		content,
+		contentBytes,
 		createdDate,
 	}: {
 		documentId: DocumentId;
 		parentVersionId: DocumentVersionId;
 		relativePath: string;
-		content: ArrayBuffer;
+		contentBytes: Uint8Array;
 		createdDate: Date;
 	}): Promise<components["schemas"]["DocumentVersion"]> {
-		let contentBytes = new Uint8Array(content);
-
 		let response = await this.client.PUT(
 			"/vaults/{vault_id}/documents/{document_id}",
 			{
@@ -113,9 +109,8 @@ export class SyncServer {
 				},
 				body: {
 					parentVersionId,
-					contentBase64: plugin.bytes_to_base64(contentBytes),
+					contentBase64: lib.bytes_to_base64(contentBytes),
 					createdDate: createdDate.toISOString(),
-					isBinary: plugin.is_binary(contentBytes),
 					relativePath,
 				},
 			}
diff --git a/plugin/src/sync-functions/sync-locally-deleted-file.ts b/plugin/src/sync-functions/sync-locally-deleted-file.ts
index f0d8507..f439e61 100644
--- a/plugin/src/sync-functions/sync-locally-deleted-file.ts
+++ b/plugin/src/sync-functions/sync-locally-deleted-file.ts
@@ -1,4 +1,3 @@
-import { TFile } from "obsidian";
 import { Database } from "src/database/database";
 import { RelativePath } from "src/database/document-metadata";
 import { SyncServer } from "src/services/sync_service";
@@ -15,7 +14,8 @@ export async function syncLocallyDeletedFile(
 
 	await syncServer.delete({
 		documentId: metadata.documentId,
-		createdDate: new Date(), // We got the event now, so it must have been deleted now
+		// We got the event now, so it must have been deleted just now
+		createdDate: new Date(),
 	});
 
 	await database.removeDocument(path);
diff --git a/plugin/src/sync-functions/sync-locally-renamed-file.ts b/plugin/src/sync-functions/sync-locally-renamed-file.ts
index cd7f4fa..d6d4bc8 100644
--- a/plugin/src/sync-functions/sync-locally-renamed-file.ts
+++ b/plugin/src/sync-functions/sync-locally-renamed-file.ts
@@ -1,6 +1,9 @@
+import * as lib from "../../../backend/sync_lib/pkg/sync_lib.js";
 import { TFile } from "obsidian";
 import { Database } from "src/database/database";
+import { Logger } from "src/logger";
 import { SyncServer } from "src/services/sync_service";
+import { hash } from "src/utils";
 
 export async function syncLocallyRenamedFile(
 	database: Database,
@@ -13,18 +16,42 @@ export async function syncLocallyRenamedFile(
 		throw `Document metadata not found for ${oldPath}`;
 	}
 
-	const response = await syncServer.update({
+	const contentBytes = new Uint8Array(await file.vault.readBinary(file));
+	const responsePromise = syncServer.update({
 		documentId: metadata.documentId,
 		parentVersionId: metadata.parentVersionId,
 		relativePath: file.path,
-		content: await file.vault.readBinary(file),
+		contentBytes,
 		createdDate: new Date(file.stat.ctime),
 	});
 
-	await database.moveDocument({
+	const contentHash = hash(contentBytes);
+	const response = await responsePromise;
+
+	const localDbUpdatePromise = database.moveDocument({
 		oldRelativePath: oldPath,
 		relativePath: file.path,
 		documentId: response.documentId,
 		parentVersionId: response.versionId,
+		hash: contentHash,
 	});
+
+	if (file.path !== response.relativePath) {
+		await file.vault.rename(file, response.relativePath);
+	}
+
+	const newContentBytes = new Uint8Array(await file.vault.readBinary(file));
+	const responseBytes = lib.base64_to_bytes(response.contentBase64);
+
+	if (contentBytes !== newContentBytes) {
+		Logger.getInstance().info(
+			`Content changed since sending original update request for ${file.path}`
+		);
+
+		const result = lib.merge(contentBytes, newContentBytes, responseBytes);
+
+		await file.vault.modifyBinary(file, result);
+	}
+
+	await localDbUpdatePromise;
 }
diff --git a/plugin/src/sync-functions/sync-locally-updated-file.ts b/plugin/src/sync-functions/sync-locally-updated-file.ts
index 43182cf..ac7cf2c 100644
--- a/plugin/src/sync-functions/sync-locally-updated-file.ts
+++ b/plugin/src/sync-functions/sync-locally-updated-file.ts
@@ -1,36 +1,13 @@
 import { TFile } from "obsidian";
 import { Database } from "src/database/database";
 import { SyncServer } from "src/services/sync_service";
+import { hash } from "src/utils";
+import { syncLocallyRenamedFile } from "./sync-locally-renamed-file";
 
 export async function syncLocallyUpdatedFile(
 	database: Database,
 	syncServer: SyncServer,
 	file: TFile
 ) {
-	const metadata = database.getDocument(file.path);
-	if (!metadata) {
-		throw `Document metadata not found for ${file.path}`;
-	}
-
-	const response = await syncServer.update({
-		documentId: metadata.documentId,
-		parentVersionId: metadata.parentVersionId,
-		relativePath: file.path,
-		content: await file.vault.readBinary(file),
-		createdDate: new Date(file.stat.ctime),
-	});
-
-	if (file.path !== response.relativePath) {
-		file.vault.rename(file, response.relativePath);
-	}
-
-	if ((await file.vault.read(file)) !== response.contentBase64) {
-		// todo - reconcile
-	}
-
-	await database.setDocument({
-		relativePath: file.path,
-		documentId: response.documentId,
-		parentVersionId: response.versionId,
-	});
+	syncLocallyRenamedFile(database, syncServer, file, file.path);
 }
diff --git a/plugin/src/sync-functions/sync-new-local-file.ts b/plugin/src/sync-functions/sync-new-local-file.ts
index 656d796..2cc6baf 100644
--- a/plugin/src/sync-functions/sync-new-local-file.ts
+++ b/plugin/src/sync-functions/sync-new-local-file.ts
@@ -1,29 +1,48 @@
+import * as lib from "../../../backend/sync_lib/pkg/sync_lib.js";
 import { TFile } from "obsidian";
 import { Database } from "src/database/database";
+import { Logger } from "src/logger.js";
 import { SyncServer } from "src/services/sync_service";
+import { hash } from "src/utils";
 
 export async function syncNewLocalFile(
 	database: Database,
 	syncServer: SyncServer,
 	file: TFile
 ) {
-	const response = await syncServer.create({
+	const contentBytes = new Uint8Array(await file.vault.readBinary(file));
+	const responsePromise = syncServer.create({
 		relativePath: file.path,
-		content: await file.vault.readBinary(file),
+		contentBytes,
 		createdDate: new Date(file.stat.ctime),
 	});
 
-	if (file.path !== response.relativePath) {
-		file.vault.rename(file, response.relativePath);
-	}
+	const contentHash = hash(contentBytes);
+	const response = await responsePromise;
 
-	if ((await file.vault.read(file)) !== response.contentBase64) {
-		// todo - reconcile
-	}
-
-	await database.setDocument({
+	const localDbUpdatePromise = database.setDocument({
 		relativePath: response.relativePath,
 		documentId: response.documentId,
 		parentVersionId: response.versionId,
+		hash: contentHash,
 	});
+
+	if (file.path !== response.relativePath) {
+		await file.vault.rename(file, response.relativePath);
+	}
+
+	const newContentBytes = new Uint8Array(await file.vault.readBinary(file));
+	const responseBytes = lib.base64_to_bytes(response.contentBase64);
+
+	if (contentBytes !== newContentBytes) {
+		Logger.getInstance().info(
+			`Content changed since sending original create request for ${file.path}`
+		);
+
+		const result = lib.merge(contentBytes, newContentBytes, responseBytes);
+
+		await file.vault.modifyBinary(file, result);
+	}
+
+	await localDbUpdatePromise;
 }