diff --git a/lib/models/LineConverter.js b/lib/models/LineConverter.js
index ff1a1c7f..cfd0856c 100644
--- a/lib/models/LineConverter.js
+++ b/lib/models/LineConverter.js
@@ -140,7 +140,9 @@ function combineText (textItems) {
     if (!text.endsWith(' ') && !textToAdd.startsWith(' ')) {
       if (lastItem) {
         const xDistance = textItem.x - lastItem.x - lastItem.width
-        if (xDistance > 5) {
+        if (xDistance > 15) {
+          text += '   '
+        } else if (xDistance > 5) {
           text += ' '
         }
       } else {
diff --git a/lib/models/transformations/ToMarkdown.js b/lib/models/transformations/ToMarkdown.js
index c8293d54..ca008640 100644
--- a/lib/models/transformations/ToMarkdown.js
+++ b/lib/models/transformations/ToMarkdown.js
@@ -21,8 +21,15 @@ module.exports = class ToMarkdown extends Transformation {
         }
 
         // Concatenate words that were previously broken up by newline
+        // (handled below per block type)
+
+        // Ensure each bullet point starts on its own line
+        concatText = concatText.replace(/ • /g, '\n• ')
+
+        // Concatenate words that were previously broken up by newline
+        // Only remove hyphens at line breaks (word continuation), not in content
         if (block.category !== 'LIST') {
-          concatText = concatText.split('- ').join('')
+          concatText = concatText.replace(/(\w)- \n(\w)/g, '$1$2')
         }
 
         // Assume there are no code blocks in our documents