diff --git a/src/engine/block.go b/src/engine/block.go
index ae01cd7c..ee2e7937 100644
--- a/src/engine/block.go
+++ b/src/engine/block.go
@@ -14,6 +14,9 @@ type BlockType string
 // BlockAlignment aligment of a Block
 type BlockAlignment string
 
+// Overflow defines how to handle a right block that overflows with the previous block
+type Overflow string
+
 const (
 	// Prompt writes one or more Segments
 	Prompt BlockType = "prompt"
@@ -25,6 +28,10 @@ const (
 	Left BlockAlignment = "left"
 	// Right aligns right
 	Right BlockAlignment = "right"
+	// Break adds a line break
+	Break Overflow = "break"
+	// Hide hides the block
+	Hide Overflow = "hide"
 )
 
 // Block defines a part of the prompt with optional segments
@@ -36,6 +43,7 @@ type Block struct {
 	Segments         []*Segment     `json:"segments,omitempty"`
 	Newline          bool           `json:"newline,omitempty"`
 	Filler           string         `json:"filler,omitempty"`
+	Overflow         Overflow       `json:"overflow,omitempty"`
 
 	env                   environment.Environment
 	writer                color.Writer
diff --git a/src/engine/engine.go b/src/engine/engine.go
index ae24dbbc..8addeb88 100644
--- a/src/engine/engine.go
+++ b/src/engine/engine.go
@@ -40,8 +40,8 @@ func (e *Engine) string() string {
 	return e.console.String()
 }
 
-func (e *Engine) canWriteRPrompt() bool {
-	if e.rprompt == "" || e.Plain {
+func (e *Engine) canWriteRPrompt(rprompt bool) bool {
+	if rprompt && (e.rprompt == "" || e.Plain) {
 		return false
 	}
 	consoleWidth, err := e.Env.TerminalWidth()
@@ -55,7 +55,10 @@ func (e *Engine) canWriteRPrompt() bool {
 		overflow := promptWidth % consoleWidth
 		availableSpace = consoleWidth - overflow
 	}
-	promptBreathingRoom := 30
+	promptBreathingRoom := 5
+	if rprompt {
+		promptBreathingRoom = 30
+	}
 	canWrite := (availableSpace - e.rpromptLength) >= promptBreathingRoom
 	return canWrite
 }
@@ -107,6 +110,15 @@ func (e *Engine) shouldFill(block *Block, length int) (string, bool) {
 }
 
 func (e *Engine) renderBlock(block *Block) {
+	defer func() {
+		// Due to a bug in Powershell, the end of the line needs to be cleared.
+		// If this doesn't happen, the portion after the prompt gets colored in the background
+		// color of the line above the new input line. Clearing the line fixes this,
+		// but can hopefully one day be removed when this is resolved natively.
+		if e.Env.Shell() == shell.PWSH || e.Env.Shell() == shell.PWSH5 {
+			e.writeANSI(e.Ansi.ClearAfter())
+		}
+	}()
 	// when in bash, for rprompt blocks we need to write plain
 	// and wrap in escaped mode or the prompt will not render correctly
 	if e.Env.Shell() == shell.BASH && (block.Type == RPrompt || block.Alignment == Right) {
@@ -135,20 +147,34 @@ func (e *Engine) renderBlock(block *Block) {
 			text, length := block.RenderSegments()
 			e.currentLineLength += length
 			e.write(text)
-			break
+			return
 		}
 
 		if block.Alignment != Right {
-			break
+			return
 		}
 
 		text, length := block.RenderSegments()
-		padText, hasPadText := e.shouldFill(block, length)
-		if hasPadText {
+		e.rpromptLength = length
+
+		if !e.canWriteRPrompt(false) {
+			switch block.Overflow {
+			case Break:
+				e.newline()
+			case Hide:
+				// make sure to fill if needed
+				if padText, OK := e.shouldFill(block, 0); OK {
+					e.write(padText)
+				}
+				return
+			}
+		}
+
+		if padText, OK := e.shouldFill(block, length); OK {
 			// in this case we can print plain
 			e.write(padText)
 			e.write(text)
-			break
+			return
 		}
 		// this can contain ANSI escape sequences
 		ansi := e.Ansi
@@ -167,13 +193,6 @@ func (e *Engine) renderBlock(block *Block) {
 	case RPrompt:
 		e.rprompt, e.rpromptLength = block.RenderSegments()
 	}
-	// Due to a bug in Powershell, the end of the line needs to be cleared.
-	// If this doesn't happen, the portion after the prompt gets colored in the background
-	// color of the line above the new input line. Clearing the line fixes this,
-	// but can hopefully one day be removed when this is resolved natively.
-	if e.Env.Shell() == shell.PWSH || e.Env.Shell() == shell.PWSH5 {
-		e.writeANSI(e.Ansi.ClearAfter())
-	}
 }
 
 // debug will loop through your config file and output the timings for each segments
@@ -231,7 +250,7 @@ func (e *Engine) print() string {
 		prompt += fmt.Sprintf("\nRPROMPT=\"%s\"", e.rprompt)
 		return prompt
 	case shell.PWSH, shell.PWSH5, shell.PLAIN, shell.NU:
-		if !e.canWriteRPrompt() {
+		if !e.canWriteRPrompt(true) {
 			break
 		}
 		e.write(e.Ansi.SaveCursorPosition())
@@ -240,7 +259,7 @@ func (e *Engine) print() string {
 		e.write(e.rprompt)
 		e.write(e.Ansi.RestoreCursorPosition())
 	case shell.BASH:
-		if !e.canWriteRPrompt() {
+		if !e.canWriteRPrompt(true) {
 			break
 		}
 		// in bash, the entire rprompt needs to be escaped for the prompt to be interpreted correctly
diff --git a/src/engine/engine_test.go b/src/engine/engine_test.go
index 81034969..710c21fa 100644
--- a/src/engine/engine_test.go
+++ b/src/engine/engine_test.go
@@ -39,7 +39,7 @@ func TestCanWriteRPrompt(t *testing.T) {
 			currentLineLength: tc.PromptLength,
 			rprompt:           "hello",
 		}
-		got := engine.canWriteRPrompt()
+		got := engine.canWriteRPrompt(true)
 		assert.Equal(t, tc.Expected, got, tc.Case)
 	}
 }
diff --git a/themes/schema.json b/themes/schema.json
index aa28f2d6..6fea2e4e 100644
--- a/themes/schema.json
+++ b/themes/schema.json
@@ -125,6 +125,29 @@
             "required": ["type", "segments"],
             "title": "RPrompt definition, contains 1 or more segments to render to the right of the cursor"
           }
+        },
+        {
+          "if": {
+            "properties": {
+              "type": {
+                "const": "prompt"
+              },
+              "alignment": {
+                "const": "right"
+              }
+            }
+          },
+          "then": {
+            "properties": {
+              "type": {
+                "type": "string",
+                "title": "Block overflow",
+                "description": "https://ohmyposh.dev/docs/configuration/block#overflow",
+                "enum": ["break", "hide"],
+                "default": ""
+              }
+            }
+          }
         }
       ],
       "properties": {
diff --git a/website/docs/configuration/block.mdx b/website/docs/configuration/block.mdx
index 6e7cf64a..af60b387 100644
--- a/website/docs/configuration/block.mdx
+++ b/website/docs/configuration/block.mdx
@@ -71,6 +71,7 @@ segments = [
 - newline: `boolean`
 - alignment: `left` | `right`
 - filler: `string`
+- overflow: `break` | `hide`
 - segments: `array` of one or more `segments`
 
 ### Type
@@ -100,6 +101,11 @@ to be repeated to this property. Add this property to the _right_ aligned block.
 "filler": "."
 ```
 
+### Overflow
+
+When the right aligned block is so long it will overflow the left aligned block, the engine will either
+break the block or hide it based on the setting. By default it is printed as is on the same line.
+
 ### Segments
 
 Array of one or more segments.