diff --git a/.changeset/brave-brackets-split.md b/.changeset/brave-brackets-split.md
new file mode 100644
index 00000000000..2c73aeab5fe
--- /dev/null
+++ b/.changeset/brave-brackets-split.md
@@ -0,0 +1,7 @@
+---
+"wrangler": patch
+---
+
+Treat bracket-quoted identifiers as quoted when splitting D1 SQL files
+
+The D1 SQL splitter handled `'`, `"` and backtick quoting but not SQLite's bracket-quoted identifiers (`[name]`), while `normalizeSqlLineEndings()` in the same file already did. A `;` inside such an identifier, e.g. `CREATE TABLE metrics ([value;unit] TEXT);`, was treated as a statement boundary, so `wrangler d1 execute --file` and `wrangler d1 migrations apply` sent broken fragments to D1. The scanner now skips over `[` … `]` like the other quote styles, which also keeps the new punctuation-delimited compound markers from matching keywords inside brackets, such as a `[end]` column in a trigger body.
diff --git a/.changeset/olive-donuts-battle.md b/.changeset/olive-donuts-battle.md
new file mode 100644
index 00000000000..45c6d5a3737
--- /dev/null
+++ b/.changeset/olive-donuts-battle.md
@@ -0,0 +1,9 @@
+---
+"wrangler": patch
+---
+
+Recognise compound statement markers that are not padded with whitespace
+
+`wrangler d1 execute --file` and `wrangler d1 migrations apply` split a SQL file into statements before sending them to D1. The splitter only recognised `BEGIN`, `CASE` and `END` when they were surrounded by whitespace, so SQL that SQLite accepts, such as a trigger body ending in `INSERT ...;END;` or a trigger declared with `WHEN (1=1)BEGIN`, was split incorrectly: statements after the trigger were swallowed into it and silently sent as a single statement.
+
+Markers are now matched when delimited by punctuation as well, while identifiers that merely end in a keyword, such as a `weekend` table, are still left alone.
diff --git a/packages/wrangler/src/__tests__/d1/splitter.test.ts b/packages/wrangler/src/__tests__/d1/splitter.test.ts
index 60e0e3866b5..15bb3058552 100644
--- a/packages/wrangler/src/__tests__/d1/splitter.test.ts
+++ b/packages/wrangler/src/__tests__/d1/splitter.test.ts
@@ -128,6 +128,17 @@ describe("splitSqlQuery()", () => {
 		`);
 	});
 
+	it("should handle bracket-quoted identifiers", ({ expect }) => {
+		expect(
+			splitSqlQuery(`
+    CREATE TABLE metrics ([value;unit] TEXT);
+    SELECT [value;unit] FROM metrics;`)
+		).toEqual([
+			"CREATE TABLE metrics ([value;unit] TEXT)",
+			"SELECT [value;unit] FROM metrics",
+		]);
+	});
+
 	it("should handle inline comments", ({ expect }) => {
 		expect(
 			splitSqlQuery(
@@ -277,6 +288,114 @@ describe("splitSqlQuery()", () => {
 		`);
 	});
 
+	it("should end a compound statement when END follows a semicolon", ({
+		expect,
+	}) => {
+		expect(
+			splitSqlQuery(`
+    CREATE TRIGGER audit_trigger AFTER INSERT ON items
+    BEGIN
+        INSERT INTO audit (item_id) VALUES (new.id);END;
+    INSERT INTO items (id) VALUES (1);
+    SELECT * FROM items;`)
+		).toEqual([
+			`CREATE TRIGGER audit_trigger AFTER INSERT ON items
+    BEGIN
+        INSERT INTO audit (item_id) VALUES (new.id);END`,
+			"INSERT INTO items (id) VALUES (1)",
+			"SELECT * FROM items",
+		]);
+	});
+
+	it("should start a compound statement when BEGIN follows a parenthesis", ({
+		expect,
+	}) => {
+		expect(
+			splitSqlQuery(`
+    CREATE TRIGGER audit_trigger AFTER INSERT ON items FOR EACH ROW WHEN (1=1)BEGIN
+        INSERT INTO audit (item_id) VALUES (new.id);
+    END;
+    SELECT * FROM items;`)
+		).toEqual([
+			`CREATE TRIGGER audit_trigger AFTER INSERT ON items FOR EACH ROW WHEN (1=1)BEGIN
+        INSERT INTO audit (item_id) VALUES (new.id);
+    END`,
+			"SELECT * FROM items",
+		]);
+	});
+
+	it("should end a CASE expression closed by a parenthesis or comma", ({
+		expect,
+	}) => {
+		expect(
+			splitSqlQuery(`
+    SELECT SUM(CASE WHEN a THEN 1 ELSE 0 END) FROM t;
+    SELECT CASE WHEN a THEN 1 ELSE 0 END, b FROM t;
+    SELECT * FROM t;`)
+		).toEqual([
+			"SELECT SUM(CASE WHEN a THEN 1 ELSE 0 END) FROM t",
+			"SELECT CASE WHEN a THEN 1 ELSE 0 END, b FROM t",
+			"SELECT * FROM t",
+		]);
+	});
+
+	it("should not treat an identifier ending in END as a compound statement end", ({
+		expect,
+	}) => {
+		expect(
+			splitSqlQuery(`
+    CREATE TABLE weekend (id INTEGER PRIMARY KEY);
+    INSERT INTO weekend (id) VALUES (1);
+    SELECT * FROM weekend;`)
+		).toEqual([
+			"CREATE TABLE weekend (id INTEGER PRIMARY KEY)",
+			"INSERT INTO weekend (id) VALUES (1)",
+			"SELECT * FROM weekend",
+		]);
+	});
+
+	it("should not treat an accented identifier ending in END as a compound statement end", ({
+		expect,
+	}) => {
+		expect(
+			splitSqlQuery(`
+    CREATE TRIGGER t AFTER INSERT ON x
+    BEGIN
+        UPDATE y SET a = 1 WHERE b = néend;
+        UPDATE z SET c = 2;
+    END;
+    SELECT 1;`)
+		).toEqual([
+			`CREATE TRIGGER t AFTER INSERT ON x
+    BEGIN
+        UPDATE y SET a = 1 WHERE b = néend;
+        UPDATE z SET c = 2;
+    END`,
+			"SELECT 1",
+		]);
+	});
+
+	it("should not treat a bracket-quoted identifier as a compound statement marker", ({
+		expect,
+	}) => {
+		expect(
+			splitSqlQuery(`
+    CREATE TRIGGER t AFTER INSERT ON items
+    BEGIN
+        UPDATE x SET [end] = 1;
+        UPDATE y SET z = 2;
+    END;
+    SELECT 1;`)
+		).toEqual([
+			`CREATE TRIGGER t AFTER INSERT ON items
+    BEGIN
+        UPDATE x SET [end] = 1;
+        UPDATE y SET z = 2;
+    END`,
+			"SELECT 1",
+		]);
+	});
+
 	it("should handle compound statements for BEGINs", ({ expect }) => {
 		expect(
 			splitSqlQuery(`
diff --git a/packages/wrangler/src/d1/splitter.ts b/packages/wrangler/src/d1/splitter.ts
index 026d3aad620..a59f9f5025f 100644
--- a/packages/wrangler/src/d1/splitter.ts
+++ b/packages/wrangler/src/d1/splitter.ts
@@ -149,6 +149,10 @@ function splitSqlIntoStatements(sql: string): string[] {
 			case "`":
 				str += char + consumeUntilMarker(iterator, char);
 				break;
+			case `[`:
+				// SQLite bracket-quoted identifiers end at the first `]`; there is no escape sequence.
+				str += char + consumeUntilMarker(iterator, `]`);
+				break;
 			case `$`: {
 				const dollarQuote =
 					"$" + consumeWhile(iterator, isDollarQuoteIdentifier);
@@ -247,16 +251,27 @@ function isDollarQuoteIdentifier(str: string) {
 	);
 }
 
+/**
+ * Compound statement markers only need to be delimited from surrounding
+ * identifiers, not padded with whitespace: SQLite accepts `WHEN (1=1)BEGIN` and
+ * `INSERT ...;END;`. The lookbehind keeps identifiers that merely end in the
+ * keyword, such as a `weekend` column, from matching; identifier characters
+ * include letters with diacritical marks, as in `isDollarQuoteIdentifier()`,
+ * so a `néend` column does not match either.
+ */
+const COMPOUND_STATEMENT_START = /(?<![\p{L}\p{N}_$])(BEGIN|CASE)\s$/iu;
+const COMPOUND_STATEMENT_END = /(?<![\p{L}\p{N}_$])END[^\p{L}\p{N}_$]$/iu;
+
 /**
  * Returns true if the `str` ends with a compound statement `BEGIN` or `CASE` marker.
  */
 function isCompoundStatementStart(str: string) {
-	return /\s(BEGIN|CASE)\s$/i.test(str);
+	return COMPOUND_STATEMENT_START.test(str);
 }
 
 /**
  * Returns true if the `str` ends with a compound statement `END` marker.
  */
 function isCompoundStatementEnd(str: string) {
-	return /\sEND[;\s]$/i.test(str);
+	return COMPOUND_STATEMENT_END.test(str);
 }