diff --git a/open-java-format/src/main/java/com/palantir/javaformat/java/JavaInputAstVisitor.java b/open-java-format/src/main/java/com/palantir/javaformat/java/JavaInputAstVisitor.java
index 4eb5b00ef..5f51b33ee 100644
--- a/open-java-format/src/main/java/com/palantir/javaformat/java/JavaInputAstVisitor.java
+++ b/open-java-format/src/main/java/com/palantir/javaformat/java/JavaInputAstVisitor.java
@@ -678,10 +678,18 @@ public Void visitBreak(BreakTree node, Void unused) {
     @Override
     public Void visitTypeCast(TypeCastTree node, Void unused) {
         sync(node);
-        builder.open(
-                plusFour,
-                BreakBehaviours.preferBreakingLastInnerLevel(true),
-                LastLevelBreakability.ACCEPT_INLINE_CHAIN);
+        // An inline chain that ends at this level must have room for the whole type before the break in front of the
+        // operand. Without IF_FIRST_LEVEL_FITS the chain measured the type up to its first break, the one after the
+        // "<" of a parameterized type, and once inlined the type itself had to take that break: "(PrivilegedAction<"
+        // at the end of one line and "String>)" on the next. The type stays breakable for the rare cast that does not
+        // fit on a line at all.
+        builder.open(OpenOp.builder()
+                .debugName("typeCast")
+                .plusIndent(plusFour)
+                .breakBehaviour(BreakBehaviours.preferBreakingLastInnerLevel(true))
+                .breakabilityIfLastLevel(LastLevelBreakability.ACCEPT_INLINE_CHAIN)
+                .partialInlineability(PartialInlineability.IF_FIRST_LEVEL_FITS)
+                .build());
         token("(");
         scan(node.getType(), null);
         token(")");
diff --git a/open-java-format/src/test/resources/com/palantir/javaformat/java/testdata/ojf-issue-60-cast-type-in-inline-chain.input b/open-java-format/src/test/resources/com/palantir/javaformat/java/testdata/ojf-issue-60-cast-type-in-inline-chain.input
new file mode 100644
index 000000000..ef55c2ccc
--- /dev/null
+++ b/open-java-format/src/test/resources/com/palantir/javaformat/java/testdata/ojf-issue-60-cast-type-in-inline-chain.input
@@ -0,0 +1,36 @@
+class TCPTransport {
+    @SuppressWarnings("removal")
+    static final Log tcpLog = Log.getLog(
+            "sun.rmi.transport.tcp", "tcp", LogStream.parseLevel(AccessController.doPrivileged((PrivilegedAction<
+                            String>)
+                    () -> System.getProperty("sun.rmi.transport.tcp.logLevel"))));
+
+  static final Level level = LogStream.parseLevel(AccessController.doPrivileged((PrivilegedAction<String>)()->System.getProperty("sun.rmi.transport.tcp.logLevel.and.some.more")));
+
+    static final Log methodReference = Log.getLog("sun.rmi.transport.tcp",
+        "tcp",
+            LogStream.parseLevel(
+                AccessController.doPrivileged(
+                    ( PrivilegedAction<String> )
+                            SomeVeryLongClassNameToFillTheLine
+                                    :: getTheTcpLogLevelProperty)));
+
+    static final Log twoTypeArguments =
+        Log.getLog("sun.rmi.transport.tcp", "tcp", LogStream.parseLevel(AccessController.doPrivileged((Function< String ,Integer >) s->
+            System.getProperty("sun.rmi.transport.tcp.logLevel.x"))));
+
+    static final Log nested = Log.getLog("sun.rmi.transport.tcp", "tcp", LogStream.parseLevel(AccessController.doPrivileged((Map<String,
+            ? extends List<Integer>>) () -> System.getProperty("sun.rmi.transport.tcp.lv"))));
+
+    static final Log qualified = Log.getLog("sun.rmi.transport.tcp", "tcp",
+            LogStream.parseLevel(AccessController.doPrivileged((java.util.function.
+                    Function<String, Integer>) s -> System.getProperty("sun.rmi.logLevel"))));
+
+    static final Log intersection = Log.getLog("sun.rmi.transport.tcp", "tcp", LogStream.parseLevel(
+            AccessController.doPrivileged((Runnable
+                    &java.io.Serializable) () -> System.getProperty("sun.rmi.transport.tcp.logLevelxx"))));
+
+    static final Log annotated = Log.getLog("sun.rmi.transport.tcp", "tcp",
+            LogStream.parseLevel(AccessController.doPrivileged((Function<@Nullable   String, Integer [ ]>)
+                    s -> System.getProperty("sun.rmi.transport.tcp.lvl"))));
+}
diff --git a/open-java-format/src/test/resources/com/palantir/javaformat/java/testdata/ojf-issue-60-cast-type-in-inline-chain.output b/open-java-format/src/test/resources/com/palantir/javaformat/java/testdata/ojf-issue-60-cast-type-in-inline-chain.output
new file mode 100644
index 000000000..c179a2667
--- /dev/null
+++ b/open-java-format/src/test/resources/com/palantir/javaformat/java/testdata/ojf-issue-60-cast-type-in-inline-chain.output
@@ -0,0 +1,47 @@
+class TCPTransport {
+    @SuppressWarnings("removal")
+    static final Log tcpLog = Log.getLog(
+            "sun.rmi.transport.tcp",
+            "tcp",
+            LogStream.parseLevel(AccessController.doPrivileged(
+                    (PrivilegedAction<String>) () -> System.getProperty("sun.rmi.transport.tcp.logLevel"))));
+
+    static final Level level = LogStream.parseLevel(AccessController.doPrivileged(
+            (PrivilegedAction<String>) () -> System.getProperty("sun.rmi.transport.tcp.logLevel.and.some.more")));
+
+    static final Log methodReference = Log.getLog(
+            "sun.rmi.transport.tcp",
+            "tcp",
+            LogStream.parseLevel(AccessController.doPrivileged(
+                    (PrivilegedAction<String>) SomeVeryLongClassNameToFillTheLine::getTheTcpLogLevelProperty)));
+
+    static final Log twoTypeArguments = Log.getLog(
+            "sun.rmi.transport.tcp",
+            "tcp",
+            LogStream.parseLevel(AccessController.doPrivileged(
+                    (Function<String, Integer>) s -> System.getProperty("sun.rmi.transport.tcp.logLevel.x"))));
+
+    static final Log nested = Log.getLog(
+            "sun.rmi.transport.tcp",
+            "tcp",
+            LogStream.parseLevel(AccessController.doPrivileged(
+                    (Map<String, ? extends List<Integer>>) () -> System.getProperty("sun.rmi.transport.tcp.lv"))));
+
+    static final Log qualified = Log.getLog(
+            "sun.rmi.transport.tcp",
+            "tcp",
+            LogStream.parseLevel(AccessController.doPrivileged(
+                    (java.util.function.Function<String, Integer>) s -> System.getProperty("sun.rmi.logLevel"))));
+
+    static final Log intersection = Log.getLog(
+            "sun.rmi.transport.tcp",
+            "tcp",
+            LogStream.parseLevel(AccessController.doPrivileged(
+                    (Runnable & java.io.Serializable) () -> System.getProperty("sun.rmi.transport.tcp.logLevelxx"))));
+
+    static final Log annotated = Log.getLog(
+            "sun.rmi.transport.tcp",
+            "tcp",
+            LogStream.parseLevel(AccessController.doPrivileged(
+                    (Function<@Nullable String, Integer[]>) s -> System.getProperty("sun.rmi.transport.tcp.lvl"))));
+}