diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index c5ded4e22dbf..c5bc664b4e6d 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -2436,8 +2436,35 @@ class Typer(@constructorOnly nestingLevel: Int = 0) extends Namer
       val capabilityProof = caughtExceptions.reduce(OrType(_, _, true))
       untpd.Block(makeCanThrow(capabilityProof), expr)
 
+  /** Graphic explanation of NotNullInfo logic:
+   *  Leftward exit indicates exceptional case
+   *  Downward exit indicates normal case
+   *
+   *           ┌─────┐
+   *           │ Try ├─────┬────────┬─────┐
+   *           └──┬──┘     ▼        ▼     │
+   *              │    ┌───────┐┌───────┐ │
+   *              │    │ Catch ││ Catch ├─┤
+   *              │    └───┬───┘└───┬───┘ │
+   *              └─┬──────┴────────┘     │
+   *                ▼                     ▼
+   *           ┌─────────┐           ┌─────────┐
+   *           │ Finally ├──────┐    │ Finally ├──┐
+   *           └────┬────┘      │    └────┬────┘  │
+   *                ▼           └─────────┴───────┴─►
+   *  exprNNInfo = Effect of the try block if completed normally
+   *  casesNNInfo = Effect of catch blocks completing normally
+   *  normalAfterCasesInfo = Exceptional try followed by normal catches
+   *  We type finalizer with normalAfterCasesInfo.retracted
+   *
+   *  Overall effect of try-catch-finally =
+   *  resNNInfo =
+   *  (exprNNInfo OR normalAfterCasesInfo) followed by normal finally block
+   *
+   *  For all nninfo, if a tree can be typed using nninfo.retractedInfo, then it can
+   *  also be typed using nninfo.
+   */
   def typedTry(tree: untpd.Try, pt: Type)(using Context): Try =
-    var nnInfo = NotNullInfo.empty
     val expr2 :: cases2x = harmonic(harmonize, pt) {
       // We want to type check tree.expr first to comput NotNullInfo, but `addCanThrowCapabilities`
       // uses the types of patterns in `tree.cases` to determine the capabilities.
@@ -2450,25 +2477,23 @@ class Typer(@constructorOnly nestingLevel: Int = 0) extends Namer
       val casesEmptyBody2 = typedCases(casesEmptyBody1, EmptyTree, defn.ThrowableType, WildcardType)
       val expr1 = typed(addCanThrowCapabilities(tree.expr, casesEmptyBody2), pt.dropIfProto)
 
-      // Since we don't know at which point the the exception is thrown in the body,
-      // we have to collect any reference that is once retracted.
-      nnInfo = expr1.notNullInfo.retractedInfo
-
-      val casesCtx = ctx.addNotNullInfo(nnInfo)
+      val casesCtx = ctx.addNotNullInfo(expr1.notNullInfo.retractedInfo)
       val cases1 = typedCases(tree.cases, EmptyTree, defn.ThrowableType, pt.dropIfProto)(using casesCtx)
       expr1 :: cases1
     }: @unchecked
     val cases2 = cases2x.asInstanceOf[List[CaseDef]]
+    val exprNNInfo = expr2.notNullInfo
+    val casesNNInfo =
+      cases2.map(_.notNullInfo)
+        .foldLeft(NotNullInfo.empty.terminatedInfo)(_.alt(_))
+    val normalAfterCasesInfo = exprNNInfo.retractedInfo.seq(casesNNInfo)
 
     // It is possible to have non-exhaustive cases, and some exceptions are thrown and not caught.
     // Therefore, the code in the finalizer and after the try block can only rely on the retracted
     // info from the cases' body.
-    if cases2.nonEmpty then
-      nnInfo = nnInfo.seq(cases2.map(_.notNullInfo.retractedInfo).reduce(_.alt(_)))
-
-    val finalizer1 = typed(tree.finalizer, defn.UnitType)(using ctx.addNotNullInfo(nnInfo))
-    nnInfo = nnInfo.seq(finalizer1.notNullInfo)
-    assignType(cpy.Try(tree)(expr2, cases2, finalizer1), expr2, cases2).withNotNullInfo(nnInfo)
+    val finalizer1 = typed(tree.finalizer, defn.UnitType)(using ctx.addNotNullInfo(normalAfterCasesInfo.retractedInfo))
+    val resNNInfo = exprNNInfo.alt(normalAfterCasesInfo).seq(finalizer1.notNullInfo)
+    assignType(cpy.Try(tree)(expr2, cases2, finalizer1), expr2, cases2).withNotNullInfo(resNNInfo)
 
   def typedTry(tree: untpd.ParsedTry, pt: Type)(using Context): Try =
     val cases: List[untpd.CaseDef] = tree.handler match
diff --git a/tests/explicit-nulls/neg/i21619.scala b/tests/explicit-nulls/neg/i21619.scala
index d7af27e3fe64..07e61e636a31 100644
--- a/tests/explicit-nulls/neg/i21619.scala
+++ b/tests/explicit-nulls/neg/i21619.scala
@@ -1,3 +1,5 @@
+class SomeException extends Exception
+
 def test1: String =
   var x: String | Null = null
   x = ""
@@ -13,6 +15,22 @@ def test1: String =
   x.replace("", "") // error
 
 def test2: String =
+  var x: String | Null = null
+  x = ""
+  var i: Int = 1
+  try
+    i match
+      case _ =>
+        x = null
+        throw new Exception()
+    x = ""
+  catch
+    case e: NoSuchMethodError =>
+      x = "e"
+  x.replace("", "") // ok
+
+// From i24296
+def test2_2: String =
   var x: String | Null = null
   x = ""
   var i: Int = 1
@@ -25,8 +43,43 @@ def test2: String =
   catch
     case e: Exception =>
       x = "e"
+    case _ =>
   x.replace("", "") // error
 
+def test2_3: String =
+  var x: String | Null = null
+  x = ""
+  var i: Int = 1
+  try
+    i match
+      case _ =>
+        x = null
+        throw new Exception()
+    x = ""
+  catch
+    case e: NoSuchMethodError =>
+      x = "e"
+    case e: AbstractMethodError =>
+      x = "e"
+  x.replace("", "") // ok
+
+def test2_4: String =
+  var x: String | Null = null
+  x = ""
+  var i: Int = 1
+  try
+    i match
+      case _ =>
+        x = null
+        throw new Exception()
+    x = ""
+  catch
+    case e: NoSuchMethodError =>
+      x = "e"
+    case e: AbstractMethodError =>
+      throw new Exception()
+  x.replace("", "") // ok
+
 def test3: String =
   var x: String | Null = null
   x = ""
@@ -89,4 +142,225 @@ def test6 = {
     }
   }
   x.replace("", "") // error
-}
\ No newline at end of file
+}
+
+// From i24296
+def test7() =
+  var x: String | Null = null
+  try {
+    x = ""
+  } catch {
+    case e =>
+      throw e
+  }
+  x.trim() // ok
+
+def test8() =
+  var x: String | Null = null
+  try {
+    try {
+      x = ""
+    } catch {
+      case e => throw e
+    }
+  } catch {
+    case e => throw e
+  }
+  x.trim() // ok
+
+def test9() =
+  var x: String | Null = null
+  try {
+    x = ""
+  } catch {
+    case e: AssertionError =>
+      throw e
+    case _ =>
+  }
+  x.trim() // error
+
+def test9_2() =
+  var x: String | Null = null
+  try {
+    x = ""
+  } catch {
+    case e: AssertionError =>
+      throw e
+  }
+  x.trim() // ok
+
+def test10() =
+  var x: String | Null = null
+  try {
+    x = ""
+  } catch {
+    case e =>
+      throw e
+  } finally {
+    x = null
+  }
+  x.trim() // error
+
+def test11() =
+  var x: String | Null = null
+  try {
+    x = ""
+  } catch {
+    case e =>
+      x = null
+      throw e
+  } finally {
+    x = ""
+  }
+  x.trim() // ok
+
+def test12() =
+  var x: String | Null = null
+  try {
+    x = ""
+  } catch {
+    case e =>
+      x = null
+      throw e
+  } finally {
+    throw new Exception
+    x = ""
+  }
+  x.trim() // ok
+
+def test12_2() =
+  var x: String | Null = null
+  try {
+    x = ""
+  } catch {
+    case e =>
+      x = null
+      throw e
+  } finally {
+    throw new Exception
+  }
+  x.trim() // ok
+
+def test13() =
+  var x: String | Null = null
+  try {
+    x = null
+    throw new RuntimeException
+  } finally {
+    x.trim() // error
+  }
+  x.trim() // OK
+
+def test14() =
+  var x: String | Null = ""
+  x = ""
+  try {
+    try {
+    } catch {
+      case e =>
+        x = null
+        throw e
+    }
+  } catch {
+    case e =>
+      x.trim() // error
+  }
+
+
+
+def test15: String =
+  var x: String | Null = ???
+  var y: String | Null = ???
+  // ...
+  try
+    x = null
+    // ...
+    x = ""
+  catch
+    case e: SomeException =>
+      x = null
+      // situation 1: don't throw or return
+      // situation 2:
+      return ""
+  finally
+    y = x
+    // should always error on y.trim
+
+  y.trim  // error (ideally, should error if situation 1, should not error if situation 2)
+
+def test16: String =
+  var x: String | Null = ???
+  x = ""
+  try
+    // call some method that throws
+    // ...
+    x = ""
+  catch
+    case e: SomeException =>
+      x = null
+      // call some method that throws
+      // ...
+      x = "<error>"
+  finally {}
+
+  x.trim() // ok
+
+def test17: String =
+  var x: String | Null = ???
+  x = ""
+  try
+    // call some method that throws
+    // ...
+    x = ""
+  catch
+    case e: SomeException =>
+      x = null
+      // call some method that throws
+      // ...
+      x = "<error>"
+  finally
+    println(x.trim()) // error
+
+  ""
+
+def test18: String =
+  var x: String | Null = ???
+  var y: String | Null = ???
+  // ...
+  try
+    x = null
+    y = null
+    // ...
+    x = ""
+    y = ""
+  catch
+    case e: SomeException =>
+      x = null
+      return ""
+  finally {}
+
+  x.trim + y.trim
+
+
+def test19: String =
+  var x: String | Null = ???
+  try
+    x = null
+  catch
+    case e: SomeException =>
+      x = null
+      throw e
+  finally
+    throw new Exception()
+  x.trim // ok
+
+def test20: String =
+  var x: String | Null = ???
+  x = ""
+  try
+    x = ""
+  catch
+    case e: SomeException =>
+      x = ""
+  finally {}
+  x.trim // ok
\ No newline at end of file