diff --git a/src/pyinfra/operations/files.py b/src/pyinfra/operations/files.py
index afbfa9fcc..b33bc0707 100644
--- a/src/pyinfra/operations/files.py
+++ b/src/pyinfra/operations/files.py
@@ -1925,7 +1925,8 @@ def block(
     + line: regex before or after which the content should be added if it doesn't exist.
     + backup: whether to backup the file (see ``files.line``). Default False.
     + escape_regex_characters: whether to escape regex characters from the matching line
-    + try_prevent_shell_expansion: tries to prevent shell expanding by values like `$`
+    + try_prevent_shell_expansion: deprecated and ignored; ``content`` is always written
+      literally (no shell expansion) and is safely shell-quoted
     + marker: the base string used to mark the text.  Default is ``# {mark} PYINFRA BLOCK``
     + begin: the value for ``{mark}`` in the marker before the content. Default is ``BEGIN``
     + end: the value for ``{mark}`` in the marker after the content. Default is ``END``
@@ -1945,8 +1946,9 @@ def block(
 
     Removal ignores ``content`` and ``line``
 
-    Preventing shell expansion works by wrapping the content in '`' before passing to `awk`.
-    WARNING: This will break if the content contains raw single quotes.
+    ``content`` is written to the file verbatim. It is shell-quoted before being passed to
+    ``awk``, so shell metacharacters (``$(...)``, quotes, backticks) are kept literal and never
+    expanded on the remote host.
 
     **Examples:**
 
@@ -1987,11 +1989,10 @@ def block(
             marker="<!-- {mark} PYINFRA BLOCK -->",
         )
 
-        # put complex alias into .zshrc
+        # put complex alias into .zshrc (written literally, no shell expansion)
         files.block(
             path="/home/user/.zshrc",
             content="eval $(thef -a)",
-            try_prevent_shell_expansion=True,
             marker="## {mark} ALIASES ##"
         )
     """
@@ -2068,15 +2069,8 @@ def block(
             # convert string to list of lines
             content = content.split("\n")
 
-        the_block = "\n".join([mark_1, *content, mark_2])
-        if try_prevent_shell_expansion:
-            the_block = f"'{the_block}'"
-            if any("'" in line for line in content):
-                logger.warning(
-                    "content contains single quotes, shell expansion prevention may fail"
-                )
-        else:
-            the_block = f'"{the_block}"'
+        block_with_markers = "\n".join([mark_1, *content, mark_2])
+        block_content = "\n".join(content)
 
         if (current is None) or ((current == []) and (before == after)):
             # a) no file or b) file but no markers and we're adding at start or end.
@@ -2090,7 +2084,7 @@ def block(
                 original if not before else " - ",
                 original if before else " - ",
                 '> "$OUT"',
-                f"<<{here}\n{the_block[1:-1]}\n{here}\n",
+                f"<<'{here}'\n{block_with_markers}\n{here}\n",
                 ")",
                 real_out,
             )
@@ -2109,7 +2103,7 @@ def block(
                 out_prep,
                 prog,
                 q_path,
-                the_block,
+                QuoteString(block_with_markers),
                 '> "$OUT"',
                 real_out,
             )
@@ -2125,11 +2119,7 @@ def block(
                     out_prep,
                     prog,
                     q_path,
-                    (
-                        '"' + "\n".join(content) + '"'
-                        if not try_prevent_shell_expansion
-                        else "'" + "\n".join(content) + "'"
-                    ),
+                    QuoteString(block_content),
                     '> "$OUT"',
                     real_out,
                 )
diff --git a/tests/operations/files.block/add_existing_block_different_content.json b/tests/operations/files.block/add_existing_block_different_content.json
index 87e26676f..a4e53991d 100644
--- a/tests/operations/files.block/add_existing_block_different_content.json
+++ b/tests/operations/files.block/add_existing_block_different_content.json
@@ -19,6 +19,6 @@
         }
     },
     "commands": [
-        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {{f=1; x=ARGV[2]; ARGV[2]=\"\"}}/# BEGIN PYINFRA BLOCK/ {print; print x; f=0} /# END PYINFRA BLOCK/ {print; f=1; next} f' /home/someone/something \"should be this\" > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
+        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {{f=1; x=ARGV[2]; ARGV[2]=\"\"}}/# BEGIN PYINFRA BLOCK/ {print; print x; f=0} /# END PYINFRA BLOCK/ {print; f=1; next} f' /home/someone/something 'should be this' > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
     ]
 }
\ No newline at end of file
diff --git a/tests/operations/files.block/add_existing_block_different_content_and_backup.json b/tests/operations/files.block/add_existing_block_different_content_and_backup.json
index f61c9e9a2..716fb459f 100644
--- a/tests/operations/files.block/add_existing_block_different_content_and_backup.json
+++ b/tests/operations/files.block/add_existing_block_different_content_and_backup.json
@@ -20,6 +20,6 @@
         }
     },
     "commands": [
-        "cp /home/someone/something /home/someone/something.a-timestamp && OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {{f=1; x=ARGV[2]; ARGV[2]=\"\"}}/# BEGIN PYINFRA BLOCK/ {print; print x; f=0} /# END PYINFRA BLOCK/ {print; f=1; next} f' /home/someone/something \"should be this\" > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
+        "cp /home/someone/something /home/someone/something.a-timestamp && OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {{f=1; x=ARGV[2]; ARGV[2]=\"\"}}/# BEGIN PYINFRA BLOCK/ {print; print x; f=0} /# END PYINFRA BLOCK/ {print; f=1; next} f' /home/someone/something 'should be this' > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
     ]
 }
\ No newline at end of file
diff --git a/tests/operations/files.block/add_existing_block_different_content_multiple_lines.json b/tests/operations/files.block/add_existing_block_different_content_multiple_lines.json
index 6bc1e7f63..ea6a71b2d 100644
--- a/tests/operations/files.block/add_existing_block_different_content_multiple_lines.json
+++ b/tests/operations/files.block/add_existing_block_different_content_multiple_lines.json
@@ -23,6 +23,6 @@
         }
     },
     "commands": [
-        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {{f=1; x=ARGV[2]; ARGV[2]=\"\"}}/# BEGIN PYINFRA BLOCK/ {print; print x; f=0} /# END PYINFRA BLOCK/ {print; f=1; next} f' /home/someone/something \"should be this\nand this\nand even this\" > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
+        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {{f=1; x=ARGV[2]; ARGV[2]=\"\"}}/# BEGIN PYINFRA BLOCK/ {print; print x; f=0} /# END PYINFRA BLOCK/ {print; f=1; next} f' /home/someone/something 'should be this\nand this\nand even this' > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
     ]
 }
\ No newline at end of file
diff --git a/tests/operations/files.block/add_no_existing_block_and_no_line.json b/tests/operations/files.block/add_no_existing_block_and_no_line.json
index 75b2c62f1..7549bb43c 100644
--- a/tests/operations/files.block/add_no_existing_block_and_no_line.json
+++ b/tests/operations/files.block/add_no_existing_block_and_no_line.json
@@ -17,6 +17,6 @@
         }
     },
     "commands": [
-        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && ( awk '{{print}}'  -  /dev/null > \"$OUT\" <<PYINFRAHERE\n# BEGIN PYINFRA BLOCK\nplease add this\n# END PYINFRA BLOCK\nPYINFRAHERE\n )  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  /home/someone/something"
+        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && ( awk '{{print}}'  -  /dev/null > \"$OUT\" <<'PYINFRAHERE'\n# BEGIN PYINFRA BLOCK\nplease add this\n# END PYINFRA BLOCK\nPYINFRAHERE\n )  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  /home/someone/something"
     ]
 }
\ No newline at end of file
diff --git a/tests/operations/files.block/add_no_existing_block_line_provided.json b/tests/operations/files.block/add_no_existing_block_line_provided.json
index 648fec0ab..a3b2f4ce3 100644
--- a/tests/operations/files.block/add_no_existing_block_line_provided.json
+++ b/tests/operations/files.block/add_no_existing_block_line_provided.json
@@ -17,6 +17,6 @@
         }
     },
     "commands": [
-        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {x=ARGV[2]; ARGV[2]=\"\"}  f!=1 && /^.*before this.*$/ { print x; f=1} END {if (f==0) print x } { print }' /home/someone/something \"# BEGIN PYINFRA BLOCK\nplease add this\n# END PYINFRA BLOCK\" > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
+        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {x=ARGV[2]; ARGV[2]=\"\"}  f!=1 && /^.*before this.*$/ { print x; f=1} END {if (f==0) print x } { print }' /home/someone/something '# BEGIN PYINFRA BLOCK\nplease add this\n# END PYINFRA BLOCK' > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
     ]
 }
\ No newline at end of file
diff --git a/tests/operations/files.block/add_no_existing_block_line_provided_escape_regex.json b/tests/operations/files.block/add_no_existing_block_line_provided_escape_regex.json
index 7c21c57dd..ee3235589 100644
--- a/tests/operations/files.block/add_no_existing_block_line_provided_escape_regex.json
+++ b/tests/operations/files.block/add_no_existing_block_line_provided_escape_regex.json
@@ -18,6 +18,6 @@
         }
     },
     "commands": [
-        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {x=ARGV[2]; ARGV[2]=\"\"}  f!=1 && /^.*before this \\*.*$/ { print x; f=1} END {if (f==0) print x } { print }' /home/someone/something \"# BEGIN PYINFRA BLOCK\nplease add this\n# END PYINFRA BLOCK\" > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
+        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  MODE=\"$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)\" && OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && awk 'BEGIN {x=ARGV[2]; ARGV[2]=\"\"}  f!=1 && /^.*before this \\*.*$/ { print x; f=1} END {if (f==0) print x } { print }' /home/someone/something '# BEGIN PYINFRA BLOCK\nplease add this\n# END PYINFRA BLOCK' > \"$OUT\"  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  && chmod \"$MODE\" /home/someone/something"
     ]
 }
\ No newline at end of file
diff --git a/tests/operations/files.block/add_no_existing_file.json b/tests/operations/files.block/add_no_existing_file.json
index e20948ff1..a990002a1 100644
--- a/tests/operations/files.block/add_no_existing_file.json
+++ b/tests/operations/files.block/add_no_existing_file.json
@@ -17,6 +17,6 @@
         }
     },
     "commands": [
-        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && ( awk '{{print}}' /dev/null  -  > \"$OUT\" <<PYINFRAHERE\n# BEGIN PYINFRA BLOCK\nplease add this\n# END PYINFRA BLOCK\nPYINFRAHERE\n )  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  /home/someone/something"
+        "OUT=\"$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)\" &&  OWNER=\"$(stat -c \"%u:%g\" /home/someone/something 2>/dev/null || stat -f \"%u:%g\" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))\" && ( awk '{{print}}' /dev/null  -  > \"$OUT\" <<'PYINFRAHERE'\n# BEGIN PYINFRA BLOCK\nplease add this\n# END PYINFRA BLOCK\nPYINFRAHERE\n )  && mv \"$OUT\" /home/someone/something  && chown \"$OWNER\" /home/someone/something  /home/someone/something"
     ]
 }
\ No newline at end of file
diff --git a/tests/operations/files.block/line_match_block_with_shell_metachars.yaml b/tests/operations/files.block/line_match_block_with_shell_metachars.yaml
new file mode 100644
index 000000000..ec072d030
--- /dev/null
+++ b/tests/operations/files.block/line_match_block_with_shell_metachars.yaml
@@ -0,0 +1,22 @@
+require_platform:
+- Darwin
+- Linux
+args:
+- /home/someone/something
+kwargs:
+  content: |-
+    alias l="lsd -la"
+    export _ZO_ECHO='1'
+    eval "$(zoxide init --cmd cd bash)"
+  line: before this
+  before: true
+facts:
+  files.Block:
+    begin=None, end=None, marker=None, path=/home/someone/something: []
+commands:
+- |-
+  OUT="$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)" &&  MODE="$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)" && OWNER="$(stat -c "%u:%g" /home/someone/something 2>/dev/null || stat -f "%u:%g" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))" && awk 'BEGIN {x=ARGV[2]; ARGV[2]=""}  f!=1 && /^.*before this.*$/ { print x; f=1} END {if (f==0) print x } { print }' /home/someone/something '# BEGIN PYINFRA BLOCK
+  alias l="lsd -la"
+  export _ZO_ECHO='"'"'1'"'"'
+  eval "$(zoxide init --cmd cd bash)"
+  # END PYINFRA BLOCK' > "$OUT"  && mv "$OUT" /home/someone/something  && chown "$OWNER" /home/someone/something  && chmod "$MODE" /home/someone/something
diff --git a/tests/operations/files.block/no_file_block_with_shell_metachars.yaml b/tests/operations/files.block/no_file_block_with_shell_metachars.yaml
new file mode 100644
index 000000000..209caebf5
--- /dev/null
+++ b/tests/operations/files.block/no_file_block_with_shell_metachars.yaml
@@ -0,0 +1,25 @@
+require_platform:
+- Darwin
+- Linux
+args:
+- /home/someone/something
+kwargs:
+  content: |-
+    alias l="lsd -la"
+    export _ZO_ECHO='1'
+    eval "$(zoxide init --cmd cd bash)"
+  before: false
+  after: false
+facts:
+  files.Block:
+    begin=None, end=None, marker=None, path=/home/someone/something: null
+commands:
+- |-
+  OUT="$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)" &&  OWNER="$(stat -c "%u:%g" /home/someone/something 2>/dev/null || stat -f "%u:%g" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))" && ( awk '{{print}}' /dev/null  -  > "$OUT" <<'PYINFRAHERE'
+  # BEGIN PYINFRA BLOCK
+  alias l="lsd -la"
+  export _ZO_ECHO='1'
+  eval "$(zoxide init --cmd cd bash)"
+  # END PYINFRA BLOCK
+  PYINFRAHERE
+   )  && mv "$OUT" /home/someone/something  && chown "$OWNER" /home/someone/something  /home/someone/something
diff --git a/tests/operations/files.block/update_block_with_shell_metachars.yaml b/tests/operations/files.block/update_block_with_shell_metachars.yaml
new file mode 100644
index 000000000..6c4dc2064
--- /dev/null
+++ b/tests/operations/files.block/update_block_with_shell_metachars.yaml
@@ -0,0 +1,21 @@
+require_platform:
+- Darwin
+- Linux
+args:
+- /home/someone/something
+kwargs:
+  content: |-
+    alias l="lsd -la"
+    export _ZO_ECHO='1'
+    eval "$(zoxide init --cmd cd bash)"
+  line: before this
+  before: true
+facts:
+  files.Block:
+    begin=None, end=None, marker=None, path=/home/someone/something:
+    - previously was something else
+commands:
+- |-
+  OUT="$(TMPDIR=_tempdir_ mktemp -t pyinfra.XXXXXX)" &&  MODE="$(stat -c %a /home/someone/something 2>/dev/null || stat -f %Lp /home/someone/something 2>/dev/null)" && OWNER="$(stat -c "%u:%g" /home/someone/something 2>/dev/null || stat -f "%u:%g" /home/someone/something 2>/dev/null || echo $(id -un):$(id -gn))" && awk 'BEGIN {{f=1; x=ARGV[2]; ARGV[2]=""}}/# BEGIN PYINFRA BLOCK/ {print; print x; f=0} /# END PYINFRA BLOCK/ {print; f=1; next} f' /home/someone/something 'alias l="lsd -la"
+  export _ZO_ECHO='"'"'1'"'"'
+  eval "$(zoxide init --cmd cd bash)"' > "$OUT"  && mv "$OUT" /home/someone/something  && chown "$OWNER" /home/someone/something  && chmod "$MODE" /home/someone/something