diff --git a/src/Fantomas.Tests/IfThenElseTests.fs b/src/Fantomas.Tests/IfThenElseTests.fs
index 6b96556151..9f80968cc1 100644
--- a/src/Fantomas.Tests/IfThenElseTests.fs
+++ b/src/Fantomas.Tests/IfThenElseTests.fs
@@ -2085,3 +2085,40 @@ then
 else
     ()
 """
+
+[<Test>]
+let ``multiline infix expression in if expression, 1584`` () =
+    formatSourceString
+        false
+        """
+        if sourceCode.EndsWith("\n")
+               && not
+                  <| formattedSourceCode.EndsWith(Environment.NewLine) then
+                return formattedSourceCode + Environment.NewLine
+            elif
+                not <| sourceCode.EndsWith("\n")
+                && formattedSourceCode.EndsWith(Environment.NewLine)
+            then
+                return formattedSourceCode.TrimEnd('\r', '\n')
+            else
+                return formattedSourceCode
+"""
+        config
+    |> prepend newline
+    |> should
+        equal
+        """
+if
+    sourceCode.EndsWith("\n")
+    && not
+       <| formattedSourceCode.EndsWith(Environment.NewLine)
+then
+    return formattedSourceCode + Environment.NewLine
+elif
+    not <| sourceCode.EndsWith("\n")
+    && formattedSourceCode.EndsWith(Environment.NewLine)
+then
+    return formattedSourceCode.TrimEnd('\r', '\n')
+else
+    return formattedSourceCode
+"""
diff --git a/src/Fantomas/CodePrinter.fs b/src/Fantomas/CodePrinter.fs
index b7edbc697f..d6cdc43c85 100644
--- a/src/Fantomas/CodePrinter.fs
+++ b/src/Fantomas/CodePrinter.fs
@@ -2269,7 +2269,7 @@ and genExpr astContext synExpr ctx =
                             indent
                             +> sepNln
                             +> genAlternativeAppWithParenthesis app astContext
-                            +> sepSpace
+                            +> ifElse (noBreakInfixOps.Contains(s)) sepSpace sepNln
                             +> genInfixOperator s e
                             +> sepSpace
                             +> genExpr astContext e2