diff --git a/CHANGELOG.md b/CHANGELOG.md
index ea193d4427..df8091cc61 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 ### Fixed
 * Indenting problem with `match` workaround for single-line stroustrup expressions [#2586](https://github.com/fsprojects/fantomas/issues/2586)
+* System.Exception: Fantomas is trying to format the input multiple times due to the detect of multiple defines. [#628](https://github.com/fsprojects/fantomas/issues/628).
 
 ## [5.1.3] - 2022-11-14
 
diff --git a/src/Fantomas.Core.Tests/CompilerDirectivesTests.fs b/src/Fantomas.Core.Tests/CompilerDirectivesTests.fs
index ec9c367d3d..8100275b88 100644
--- a/src/Fantomas.Core.Tests/CompilerDirectivesTests.fs
+++ b/src/Fantomas.Core.Tests/CompilerDirectivesTests.fs
@@ -2983,3 +2983,85 @@ let ``dead code in active block`` () =
 b
 #endif
 """
+
+[<Test>]
+let ``dont delete #if attr in "and" type, 628`` () =
+    formatSourceStringWithDefines
+        [ "NET2" ]
+        """
+#if NET2
+[<Attr1>]
+#else
+[<Attr2>]
+#endif
+[<NoComparison>]
+type internal T1 = T1
+and [<NoComparison>]
+#if NET2
+[<Attr1>]
+#else
+[<Attr2>]
+#endif
+    internal T2 = T2
+"""
+        config
+    |> prepend newline
+    |> should
+        equal
+        """
+#if NET2
+[<Attr1>]
+#else
+#endif
+[<NoComparison>]
+type internal T1 = T1
+
+and [<NoComparison>]
+#if NET2
+[<Attr1>]
+#else
+#endif
+internal T2 = T2
+"""
+
+[<Test>]
+let ``attributes with directives in "and" type, 628`` () =
+    formatSourceString
+        false
+        """
+#if NET2
+[<Attr1>]
+#else
+[<Attr2>]
+#endif
+[<NoComparison>]
+type internal T1 = T1
+and [<NoComparison>]
+#if NET2
+[<Attr1>]
+#else
+[<Attr2>]
+#endif
+    internal T2 = T2
+"""
+        config
+    |> prepend newline
+    |> should
+        equal
+        """
+#if NET2
+[<Attr1>]
+#else
+[<Attr2>]
+#endif
+[<NoComparison>]
+type internal T1 = T1
+
+and [<NoComparison>]
+#if NET2
+[<Attr1>]
+#else
+[<Attr2>]
+#endif
+internal T2 = T2
+"""
diff --git a/src/Fantomas.Core/CodePrinter.fs b/src/Fantomas.Core/CodePrinter.fs
index 9890c98d1f..42da2b98c4 100644
--- a/src/Fantomas.Core/CodePrinter.fs
+++ b/src/Fantomas.Core/CodePrinter.fs
@@ -482,10 +482,14 @@ and genOnelinerAttributes ats =
 /// Try to group attributes if they are on the same line
 /// Separate same-line attributes by ';'
 /// Each bucket is printed in a different line
-and genAttributes (ats: SynAttributes) =
-    colPost sepNlnUnlessLastEventIsNewline sepNln ats (fun a ->
-        (genAttributesCore a.Attributes |> genTriviaFor SynAttributeList_ a.Range)
-        +> sepNlnWhenWriteBeforeNewlineNotEmpty)
+and genAttributes' nlnAfterOneliner (ats: SynAttributes) =
+    let addNln = nlnAfterOneliner || ats.Length > 1
+
+    colPost (ifElse addNln sepNlnUnlessLastEventIsNewline sepSpace) sepNln ats (fun a ->
+        let expr = genAttributesCore a.Attributes |> genTriviaFor SynAttributeList_ a.Range
+        expr)
+
+and genAttributes (ats: SynAttributes) = genAttributes' true ats
 
 and genPreXmlDoc (PreXmlDoc(lines, _)) =
     colPost sepNln sepNln lines (sprintf "///%s" >> (!-))
@@ -2916,7 +2920,7 @@ and genTypeDefn (TypeDef(ats, px, leadingKeyword, ao, tds, tcs, equalsRange, tdr
     let genLeadingKeyword =
         match leadingKeyword with
         | SynTypeDefnLeadingKeyword.Type mType -> genAttributes ats +> genTriviaFor SynTypeDefn_Type mType !- "type "
-        | SynTypeDefnLeadingKeyword.And mAnd -> genTriviaFor SynTypeDefn_And mAnd !- "and " +> genOnelinerAttributes ats
+        | SynTypeDefnLeadingKeyword.And mAnd -> genTriviaFor SynTypeDefn_And mAnd !- "and " +> genAttributes' false ats
         | SynTypeDefnLeadingKeyword.StaticType _
         | SynTypeDefnLeadingKeyword.Synthetic -> sepNone
 
diff --git a/src/Fantomas.Core/Context.fs b/src/Fantomas.Core/Context.fs
index 77554bcb26..9d8738f093 100644
--- a/src/Fantomas.Core/Context.fs
+++ b/src/Fantomas.Core/Context.fs
@@ -1045,7 +1045,7 @@ let sepSemi (ctx: Context) =
 let ifAlignBrackets f g =
     ifElseCtx (fun ctx -> ctx.Config.MultilineBlockBracketsOnSameColumn) f g
 
-let printTriviaContent (c: TriviaContent) (ctx: Context) =
+let printTriviaContent (c: TriviaContent) addBefore (ctx: Context) =
     let currentLastLine = ctx.WriterModel.Lines |> List.tryHead
 
     // Some items like #if or Newline should be printed on a newline
@@ -1073,11 +1073,18 @@ let printTriviaContent (c: TriviaContent) (ctx: Context) =
         +> ifElse after sepNlnForTrivia sepNone
     | Newline -> (ifElse addNewline (sepNlnForTrivia +> sepNlnForTrivia) sepNlnForTrivia)
     | Directive s
-    | Comment(CommentOnSingleLine s) -> (ifElse addNewline sepNlnForTrivia sepNone) +> !-s +> sepNlnForTrivia
+    | Comment(CommentOnSingleLine s) ->
+        (ifElse addNewline sepNlnForTrivia sepNone)
+        +> !-s
+        +> (ifElse addBefore sepNlnForTrivia sepNone)
     <| ctx
 
 let printTriviaInstructions (triviaInstructions: TriviaInstruction list) =
-    col sepNone triviaInstructions (fun { Trivia = trivia } -> printTriviaContent trivia.Item)
+    col
+        sepNone
+        triviaInstructions
+        (fun { Trivia = trivia
+               AddBefore = addBefore } -> printTriviaContent trivia.Item addBefore)
 
 let enterNodeFor (mainNodeName: FsAstType) (range: Range) (ctx: Context) =
     match Map.tryFind mainNodeName ctx.TriviaBefore with
diff --git a/src/Fantomas.Core/Trivia.fs b/src/Fantomas.Core/Trivia.fs
index 6d680f33d4..c4967b1e16 100644
--- a/src/Fantomas.Core/Trivia.fs
+++ b/src/Fantomas.Core/Trivia.fs
@@ -246,22 +246,41 @@ let triviaBeforeOrAfterEntireTree (rootNode: TriviaNode) (trivia: Trivia) : Triv
       AddBefore = isBefore }
 
 /// Try to put the trivia on top of the closest node
+/// (or after closest node before in some special cases)
 /// If that didn't work put it after the last node
 let simpleTriviaToTriviaInstruction (containerNode: TriviaNode) (trivia: Trivia) : TriviaInstruction option =
-    containerNode.Children
-    |> Array.tryFind (fun node -> node.Range.StartLine > trivia.Range.StartLine)
-    |> Option.map (fun node ->
+    let childrenTypes = containerNode.Children |> Array.map (fun n -> n.Type)
+
+    let mkTriviaNode addBefore (node: TriviaNode) =
         { Trivia = trivia
           Type = node.Type
           Range = node.Range
-          AddBefore = true })
+          AddBefore = addBefore }
+
+    let findChildNodeToAddAfter mainType prevType =
+        containerNode.Children
+        |> Array.indexed
+        |> Array.rev
+        |> Seq.tryFind (fun (i, node) ->
+            node.Type = mainType
+            && node.Range.StartLine < trivia.Range.StartLine
+            && childrenTypes[0 .. i - 1] |> Array.contains prevType)
+        |> Option.map snd
+
+    let addAfterNode =
+        match trivia.Item with
+        | Directive _ ->
+            // link directive after attribute for "... and ..." type
+            findChildNodeToAddAfter FsAstType.SynAttributeList_ FsAstType.SynTypeDefn_And
+        | _ -> None
+
+    addAfterNode
+    |> Option.map (mkTriviaNode false)
     |> Option.orElseWith (fun () ->
-        Array.tryLast containerNode.Children
-        |> Option.map (fun node ->
-            { Trivia = trivia
-              Type = node.Type
-              Range = node.Range
-              AddBefore = false }))
+        containerNode.Children
+        |> Array.tryFind (fun node -> node.Range.StartLine > trivia.Range.StartLine)
+        |> Option.map (mkTriviaNode true)
+        |> Option.orElseWith (fun () -> Array.tryLast containerNode.Children |> Option.map (mkTriviaNode false)))
 
 /// Try and find the smallest possible node
 let lineCommentAfterSourceCodeToTriviaInstruction