diff --git a/internal/tui/components/chat/editor/editor.go b/internal/tui/components/chat/editor/editor.go
index 7f06e69a388e10a49cbb792d0f4b8d231613eb3b..4e5f0bc431eb466cea5c6c7d436234c7a5e8531b 100644
--- a/internal/tui/components/chat/editor/editor.go
+++ b/internal/tui/components/chat/editor/editor.go
@@ -162,9 +162,7 @@ func (m *editorCmp) send() tea.Cmd {
 }
 
 func (m *editorCmp) repositionCompletions() tea.Msg {
-	cur := m.textarea.Cursor()
-	x := cur.X + m.x // adjust for padding
-	y := cur.Y + m.y + 1
+	x, y := m.completionsPosition()
 	return completions.RepositionCompletionsMsg{X: x, Y: y}
 }
 
@@ -191,32 +189,37 @@ func (m *editorCmp) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 			return m, nil
 		}
 		if item, ok := msg.Value.(FileCompletionItem); ok {
+			word := m.textarea.Word()
 			// If the selected item is a file, insert its path into the textarea
 			value := m.textarea.Value()
-			value = value[:m.completionsStartIndex]
-			value += item.Path
+			value = value[:m.completionsStartIndex] + // Remove the current query
+				item.Path + // Insert the file path
+				value[m.completionsStartIndex+len(word):] // Append the rest of the value
+			// XXX: This will always move the cursor to the end of the textarea.
 			m.textarea.SetValue(value)
+			m.textarea.MoveToEnd()
 			if !msg.Insert {
 				m.isCompletionsOpen = false
 				m.currentQuery = ""
 				m.completionsStartIndex = 0
 			}
-			return m, nil
 		}
 	case openEditorMsg:
 		m.textarea.SetValue(msg.Text)
 		m.textarea.MoveToEnd()
 	case tea.KeyPressMsg:
+		cur := m.textarea.Cursor()
+		curIdx := m.textarea.Width()*cur.Y + cur.X
 		switch {
 		// Completions
 		case msg.String() == "/" && !m.isCompletionsOpen &&
-			// only show if beginning of prompt, or if previous char is a space:
-			(len(m.textarea.Value()) == 0 || m.textarea.Value()[len(m.textarea.Value())-1] == ' '):
+			// only show if beginning of prompt, or if previous char is a space or newline:
+			(len(m.textarea.Value()) == 0 || unicode.IsSpace(rune(m.textarea.Value()[len(m.textarea.Value())-1]))):
 			m.isCompletionsOpen = true
 			m.currentQuery = ""
-			m.completionsStartIndex = len(m.textarea.Value())
+			m.completionsStartIndex = curIdx
 			cmds = append(cmds, m.startCompletions)
-		case m.isCompletionsOpen && m.textarea.Cursor().X <= m.completionsStartIndex:
+		case m.isCompletionsOpen && curIdx <= m.completionsStartIndex:
 			cmds = append(cmds, util.CmdHandler(completions.CloseCompletionsMsg{}))
 		}
 		if key.Matches(msg, DeleteKeyMaps.AttachmentDeleteMode) {
@@ -253,6 +256,7 @@ func (m *editorCmp) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 		}
 		if key.Matches(msg, m.keyMap.Newline) {
 			m.textarea.InsertRune('\n')
+			cmds = append(cmds, util.CmdHandler(completions.CloseCompletionsMsg{}))
 		}
 		// Handle Enter key
 		if m.textarea.Focused() && key.Matches(msg, m.keyMap.SendMessage) {
@@ -284,12 +288,18 @@ func (m *editorCmp) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 					// XXX: wont' work if editing in the middle of the field.
 					m.completionsStartIndex = strings.LastIndex(m.textarea.Value(), word)
 					m.currentQuery = word[1:]
+					x, y := m.completionsPosition()
+					x -= len(m.currentQuery)
 					m.isCompletionsOpen = true
-					cmds = append(cmds, util.CmdHandler(completions.FilterCompletionsMsg{
-						Query:  m.currentQuery,
-						Reopen: m.isCompletionsOpen,
-					}))
-				} else {
+					cmds = append(cmds,
+						util.CmdHandler(completions.FilterCompletionsMsg{
+							Query:  m.currentQuery,
+							Reopen: m.isCompletionsOpen,
+							X:      x,
+							Y:      y,
+						}),
+					)
+				} else if m.isCompletionsOpen {
 					m.isCompletionsOpen = false
 					m.currentQuery = ""
 					m.completionsStartIndex = 0
@@ -302,6 +312,16 @@ func (m *editorCmp) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 	return m, tea.Batch(cmds...)
 }
 
+func (m *editorCmp) completionsPosition() (int, int) {
+	cur := m.textarea.Cursor()
+	if cur == nil {
+		return m.x, m.y + 1 // adjust for padding
+	}
+	x := cur.X + m.x
+	y := cur.Y + m.y + 1 // adjust for padding
+	return x, y
+}
+
 func (m *editorCmp) Cursor() *tea.Cursor {
 	cursor := m.textarea.Cursor()
 	if cursor != nil {
@@ -382,9 +402,7 @@ func (m *editorCmp) startCompletions() tea.Msg {
 		})
 	}
 
-	cur := m.textarea.Cursor()
-	x := cur.X + m.x // adjust for padding
-	y := cur.Y + m.y + 1
+	x, y := m.completionsPosition()
 	return completions.OpenCompletionsMsg{
 		Completions: completionItems,
 		X:           x,
diff --git a/internal/tui/components/completions/completions.go b/internal/tui/components/completions/completions.go
index ab29d900010bb2a80e4e2b7d6135e44f6486769c..aad5dc8c83c163712a4d9b56e7a6442ce2380f25 100644
--- a/internal/tui/components/completions/completions.go
+++ b/internal/tui/components/completions/completions.go
@@ -27,6 +27,8 @@ type OpenCompletionsMsg struct {
 type FilterCompletionsMsg struct {
 	Query  string // The query to filter completions
 	Reopen bool
+	X      int // X position for the completions popup
+	Y      int // Y position for the completions popup
 }
 
 type RepositionCompletionsMsg struct {
@@ -165,6 +167,7 @@ func (c *completionsCmp) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 		}
 	case RepositionCompletionsMsg:
 		c.x, c.y = msg.X, msg.Y
+		c.adjustPosition()
 	case CloseCompletionsMsg:
 		c.open = false
 		return c, util.CmdHandler(CompletionsClosedMsg{})
@@ -216,15 +219,9 @@ func (c *completionsCmp) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 		cmds = append(cmds, c.list.Filter(msg.Query))
 		items := c.list.Items()
 		itemsLen := len(items)
-		width := listWidth(items)
-		c.lastWidth = c.width
-		if c.x < 0 || width < c.lastWidth {
-			c.x = c.xorig
-		} else if c.x+width >= c.wWidth {
-			c.x = c.wWidth - width - 1
-		}
-		c.width = width
-		c.height = max(min(maxCompletionsHeight, itemsLen), 1)
+		c.xorig = msg.X
+		c.x, c.y = msg.X, msg.Y
+		c.adjustPosition()
 		cmds = append(cmds, c.list.SetSize(c.width, c.height))
 		if itemsLen == 0 {
 			cmds = append(cmds, util.CmdHandler(CloseCompletionsMsg{}))
@@ -237,6 +234,20 @@ func (c *completionsCmp) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 	return c, nil
 }
 
+func (c *completionsCmp) adjustPosition() {
+	items := c.list.Items()
+	itemsLen := len(items)
+	width := listWidth(items)
+	c.lastWidth = c.width
+	if c.x < 0 || width < c.lastWidth {
+		c.x = c.xorig
+	} else if c.x+width >= c.wWidth {
+		c.x = c.wWidth - width - 1
+	}
+	c.width = width
+	c.height = max(min(maxCompletionsHeight, itemsLen), 1)
+}
+
 // View implements Completions.
 func (c *completionsCmp) View() string {
 	if !c.open || len(c.list.Items()) == 0 {
diff --git a/internal/tui/tui.go b/internal/tui/tui.go
index 1cdc0c38243da39b2bd8c8eb276beea78f1dd37f..770e7b26945e9bf7109f3076e1ad95a1f24aa51a 100644
--- a/internal/tui/tui.go
+++ b/internal/tui/tui.go
@@ -116,7 +116,8 @@ func (a *appModel) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 		return a, a.handleWindowResize(msg.Width, msg.Height)
 
 	// Completions messages
-	case completions.OpenCompletionsMsg, completions.FilterCompletionsMsg, completions.CloseCompletionsMsg, completions.RepositionCompletionsMsg:
+	case completions.OpenCompletionsMsg, completions.FilterCompletionsMsg,
+		completions.CloseCompletionsMsg, completions.RepositionCompletionsMsg:
 		u, completionCmd := a.completions.Update(msg)
 		a.completions = u.(completions.Completions)
 		return a, completionCmd